Tandem mass spectrometry approaches for recognition of isomeric compounds mixtures.

The present review aims to collect the published literature pertaining the recognition of isobaric compounds (isomers or stereoisomers) using the features of tandem mass spectrometry (MS) experiments without any chromatographic separation or chemical modification (derivatization or isotopic enrichment) of the analytes. MS/MS methods possess high selectivity, wide dynamic range and high throughput capabilities. Generally, tandem MS has limited capability for distinguishing isomers that fragment similarly. However, some MS/MS methods have been developed and positively applied to isomers discrimination. Among the literature on this topic, the applications that fit on the review subject can be summarized as follow: (1) chiral discrimination by the kinetic method, (2) the use energy-resolved tandem mass spectra and the survival yield (SY) representation, (3) the kinetics evaluation of the ion-molecule interaction and (4) the postprocessing mathematical algorithm to resolve the isomers in MS/MS signal.

Optimization and validation of the kinetic spectrophotometric method for quantitative determination of the pesticide atrazine and its application in infant formulae and cereal-based baby food.

BACKGROUND: Pesticides are potentially toxic to humans and can produce both acute and chronic health effects, depending on the quantity and the ways in which a person is exposed. Exposure to pesticides can cause serious health problems. Infants and young children are particularly sensitive to these contaminants because their brains and organ systems are not fully developed. For this reason, it is important to determine the quantities of pesticides in baby food. RESULTS: The aim of this study was to develop a kinetic-spectrophotometric method for atrazine determination and to apply it to determine pesticide in baby-food samples, using solid-phase extraction (SPE) followed by the kinetic-spectrophotometric method and the high-performance liquid chromatography (HPLC) method. This method is based on the inhibition effect of atrazine (the oxidation of sulfanilic acid (SA) by hydrogen peroxide in the alkaline medium in the presence of the Co2+ ion). Under the experimental conditions used, atrazine showed a linear dynamic range of 0.5 to 5.0 µg mL-1 , and from 5.0 to 70.00 µg mL-1 with relative standard deviations (RSD) from 1.91% to 9.41%. The limit of detection and the limit of quantification were 0.074 and 0.225 µg mL-1 , respectively. The kinetic method was successfully applied to determine the atrazine concentration in spiked samples after SPE of samples. High-performance liquid chromatography was used to verify the results. CONCLUSION: The proposed method is highly sensitive, simple, easy, requires cheap reagents, and leads to good recovery levels. It is linear, precise, and accurate. It can be used successfully for the routine analysis of atrazine in infant formulae and cereal-based food samples. © 2019 Society of Chemical Industry.

Proton affinities and ion enthalpies.

Proton affinities of a number of alkyl acetates (CH3-C(=O)-OR) and of methyl alkanoates (R-C(=O)-OCH3, R=H, alkyl) have been assembled from the literature or measured using the kinetic method. It was observed that the proton affinities for the isomeric species CH3-C(=O)-OR and R-C(=O)-OCH3 are almost identical, an unexpected result as the charge in these protonated ester molecules is largely at the keto carbon atom and so this site should be more sensitive to alkyl substitution. Analysis of the data, including those from lone pair ionisation and core-electron ionisation experiments available from the literature, indicate that after protonation, extensive charge relaxation (or polarisation) takes place (as is also the case, according to the literature, after core-electron ionisation). By contrast, after lone pair ionisation, which results in radical cations, such relaxation processes are relatively less extensive. As a consequence, changes in ion enthalpies of these protonated molecules follow more closely the changes in neutral enthalpies, compared with changes in enthalpies of the corresponding radical cations, formed by electron detachment. Preliminary analyses of published energetic data indicate that the above finding for organic esters may well be another example of a more general phenomenon.

Development of a rapid assay for ß-etherase activity using a novel chromogenic substrate.

Biocatalytic processes play a crucial role in the valorization of lignin; therefore, methods enabling the monitoring of enzymes such as ß-etherases, capable of breaking ß-O-4 aryl-ether bonds, are of significant biotechnological interest. A novel method for quantifying ß-etherase activity was developed based on the ß-ester bond formation between a chromophore and acetovainillone. The chromogenic substrate ß-(ρ-nitrophenoxy)-α-acetovanillone (PNPAV), was chemically synthesized. Kintetic monitoring of ρ-nitrophenolate release at 410 nm over 10 min, using recombinant LigF from Sphingobium sp SYK-6, LigF-AB and LigE-AB from Althererytrobacter sp B11, yielded enzimatic activities of 404. 3 mU/mg, 72 mU/mg, and 50 mU/mg, respectively. This method is applicable in a pH range of 7.0-9.0, with a sensitivity of up to 50 ng of enzyme, exhibiting no interference with lipolytic, glycolytic, proteolytic, and oxidoreductase enzymes.

Experimental determination and QSAR analysis of the rate constants for SO5•- reactions with aromatic micropollutants in water.

S(IV)-based systems used for advanced oxidation processes (AOPs) have been constructed for the degradation of organic contaminants via oxysulfur radicals, including SO3•-, SO4•-, and SO5•-. Although SO5•- is proposed as an active species in AOPs processes, research on the reactivity of SO5•- has remained unclear. In this work, 53 target aromatic micropollutants (AMPs), including 13 phenols, 27 amines, and 13 PPCPs were selected to determine the second-order reaction rate constants for SO5•- using the competitive kinetics method, in which the [Formula: see text] values, observed at pH 4 ranged from (2.44 ± 0.00) × 105 M-1 s-1 to (4.41 ± 0.28) × 107 M-1 s-1. Quantitative structure-activity relationship (QSAR) models for the oxidation of AMPs by SO5•- were developed based on 40 [Formula: see text] values of amines and phenols, and their molecular descriptors, using the stepwise multiple linear regression method. This comprehensive model exhibited the excellent goodness-of-fit (Radj2 = 0.802), robustness (QLOO2 = 0.749), and predictability (Qext2 = 0.656), and the one-electron oxidation potential (Eox), energy of the highest occupied molecular orbital energy (EHOMO), and most positive net atomic charge on the carbon atoms (qC+) were considered the most influential descriptors for the comprehensive model, indicating that SO5•- oxidizes pollutants via single electron transfer reaction and exhibits a strong oxidation capacity, especially for pollutants containing electron-donating groups. Moreover, the [Formula: see text] values of 13 PPCPs were predicted using this comprehensive model, which suggested the practical application significance of the QSAR model. This study emphasizes the direct oxidation capacity of SO5•-, which is important to evaluate and simulate AOPs based on S(IV).

Glucose Interference in Serum and Urine Samples with Various Creatinine Concentrations Measured by the Jaffe Kinetic Method.

Background: The effect of glucose interference on creatinine measurement by Jaffe kinetic method differs between serum and urine specimens. We investigated the effects of creatinine concentration and specimen dilution on glucose interference with urine creatinine measurement. Methods: Leftover serum and urine specimens were collected and stored at -20°C until study. Serum specimens were mixed to make 5 glucose concentrations ranging from <5.6 to 27.8 mmol/L, each group consisting of 5 levels of creatinine concentration ranging from <45 to 354 µmol/L. Urine specimens were divided into 5 groups of creatinine concentration ranging from <1,769 to >7956 µmol/L, each sample was spiked with glucose powder to produce 5 aliquots with glucose concentrations ranging from 0 to 666 mmol/L. Urine samples were automatically diluted 1:20 before analysis. Percent interference of creatinine measurement by Jaffe kinetic method was calculated using enzymatic method as the reference. Results: A total of 148 serum samples and 335 urine samples were analyzed. In serum, glucose interference with Jaffe creatinine measurement was found if creatinine concentrations were 177 µmol/L or less, corresponding to 3,540 µmol/L or less in urine specimens prior to 1:20 dilution. The degree of interference was greater when glucose concentration was higher or creatinine concentration was lower. Conclusions: When creatinine concentration and specimen dilution were considered, the effects of glucose interference on Jaffe creatinine measurement were similar in serum and urine specimens, and was found when creatinine concentrations in serum or diluted urine were 177 µmol/L or less.

Modification of Jaffe's kinetic method decreases bilirubin interference: A preliminary report.

The negative interference of bilirubin on serum creatinine determined by the kinetic alkaline picrate (Jaffe) reaction is the unresolved problem. Though high performance liquid chromatography and gas chromatography with mass spectroscopy have been proposed to be gold standards for creatinine estimation but they are not readily available in most of the clinical chemistry laboratories due to economic and technical constraints. Most of the present day analyzers use Jaffe's kinetic method without deproteinization. Though enzymatic methods are now routinely used as most accurate method but they are not acceptable due to cost constraints. Hence this study was planned to find out a possible solution to the problem of bilirubin interference by a minor modification in the commonly used Jaffe method so that it is amenable for use on the currently used analyzers.

Study on the Pyrolysis Kinetics and Mechanisms of the Tread Compounds of Silica-Filled Discarded Car Tires.

The disposal of used automobile tires is a major waste concern. Simply stacking tires and allowing them to decompose will harbor breeding mosquitoes that spread viruses, whereas burning them will release acidic and toxic gases. Therefore, one viable option is pyrolysis, where elevated temperatures are used to facilitate the decomposition of a material. However, the lack of theoretical support for pyrolysis technology limits the development of the pyrolysis industry when it comes to discarded tires. The purpose of this research is to put forward a brand-new multi-kinetic research method for studying materials with complex components through the discussion of various kinetic research methods. The characteristic of this kinetic research method is that it is a relatively complete theoretical system and can accurately calculate the three kinetic factors considered during the pyrolysis of multicomponent materials. The results show that the multi-kinetic research method can obtain the kinetic equation and reaction mechanism for the pyrolysis of tires with high accuracy. The pyrolysis process of this compound was divided into two stages, Reaction I and II, where the kinetic equation of Reaction I was f ( α ) = 0.2473 α - 3.0473 , with an activation energy of 155.26 kJ/mol and a pre-exponential factor of 5.88 × 109/min. Meanwhile, the kinetic equation of Reaction II was f ( α ) = 0.4142 ( 1 - α ) [ - ln ( 1 - α ) ] - 1.4143 , while its activation energy was 315.40 kJ/mol and its pre-exponential factor was 7.86 × 1017/min. Furthermore, based on the results of the research analysis, the reaction principles corresponding to Reaction I and Reaction II in the pyrolysis process of this compound were established.

Estimation of plasma haemoglobin by a modified kinetic method using o-tolidine.

Measurement of plasma hemoglobin is useful in variety of clinical conditions. In the present study we have developed a kinetic method to estimate plasma haemoglobin by using o-tolidine. This method is sensitive, rapid, economical, simple and less influenced by interfering substances. It measures plasma haemoglobin in the range of 6 to 400 mg/L (normal range < 50 mg/L) in less than two minutes and can be easily automated.

Development of a Post-Column Liquid Chromatographic Chiral Addition Method for the Separation and Resolution of Common Mammalian Monosaccharides.

The first solely MS-based methodology for the identification and resolution of the ten common mammalian monosaccharides is presented. Based on Cooks' fixed ligand kinetic method, this technique is effective on multiple classes of monosaccharides and includes the first example of two fixed ligand combinations used in a single multiplexed experiment. Subsequently, a post-HPLC chiral addition method is used in conjunction with this newly developed MS methodology for the separation and identification of mixtures of common neutral mammalian monosaccharides. This proposed technique is able to overcome a limitation of present carbohydrate analysis methods, namely the simultaneous isomeric resolution of multiple monosaccharides in a mixture. Graphical Abstract.

Extended kinetic method and RRKM modeling to reinvestigate proline's proton affinity and approach the meaning of effective temperature.

Proline proton affinity PA(Pro) was previously measured by extended kinetic methods with several amines as reference bases using a triple quadrupole mass spectrometer ( J Mass Spectrom 2005; 40: 1300). The measured value of 947.5 ± 5 kJ.mol-1 differs by more than 10 kJ.mol-1 from previous reported experimental or calculated values. This difference may be explained in part by the existence of relatively large entropy difference between the two dissociation channels (ΔΔS‡avg = 31 ± 10 J.mol-1.K-1) and by the inaccuracy of the amines proton affinity used as reference bases. In the present work, these experimental measurements were reinvestigated by RRKM modeling using MassKinetics software. From this modeling, a new PA value of 944.5 ± 5 kJ.mol-1 and a ΔΔS‡avg(600K) value of 33 ± 10 J.mol-1.K-1 are determined. However, the difference between experiment and recent theoretical calculations remains large (10 kJ.mol-1). These RRKM simulations allow also accessing to the effective temperature parameter (T eff) and to discuss the meaning of this term. As previously reported, T eff mainly depends on the internal energy and on the decomposition time as well. It also depends on the critical energies and on the transition state. Considering the entrance of the collision cell as a new ion source, T eff is finally shown to be close to a characteristic temperature (T char).

Alternated Branching Ratios by Anomaly in Collision-Induced Dissociation of Proton-Bound Hoogsteen Base Pairs of 1-Methylcytosine with 1-Methylguanine and 9-Methylguanine.

A comparative study on the proton-bound complexes of 1-methylcytosine (1-mC) with 1-methylguanine (1-mG) and 9-methylguanine (9-mG), [1-mC:1-mG:H]+ and [1-mC:9-mG:H]+, respectively, was carried out using energy-resolved collision-induced dissociation (ER-CID) experiments in combination with quantum chemical calculations. In ER-CID experiments, the measured survival yields indicated an essentially identical stability for the two proton-bound complexes. In comparison with the lowest-energy structures and base-pairing energetics predicted at the B3LYP/6-311+G(2d,2p) theory level, both complexes produced in this study were suggested to be proton-bound Hoogsteen base pairs. Curiously, despite the similarity in structures, binding energetics, and potential energy surfaces predicted by the B3LYP theory, the fragment branching ratios exhibited an intriguing alternation between the two proton-bound Hoogsteen base pairs. The CID of [1-mC:1-mG:H]+ produced protonated cytosines, [1-mC:H]+, more abundantly than [1-mG:H]+, whereas that of [1-mC:9-mG:H]+ gave rise to a more pronounced production of protonated guanines, [9-mG:H]+. However, using the proton affinities of moieties predicted by the high-accuracy methods, including CBS-QB3 and the Guassian-4 theory, the anomaly known for [Cytosine:Guanine:H]+ (J. Am. Soc. Mass Spectrom. 29, 2368-2379 (2018)) successfully accounted for the alternated branching ratios. Thereby, the anomaly, more specifically, the production of proton-transferred fragments of O-protonated cytosines in the CID of proton-bound Hoogsteen base pairs, is indeed real, which is disclosed as the alternated branching ratios in the CID spectra of [1-mC:1-mG:H]+ and [1-mC:9-mG:H]+ in this study. Graphical Abstract .

Interrogating Proton Affinities of Organophosphonate Species Via Atmospheric Flow Tube Mass Spectrometry and Computational Methods.

Within trace vapor analysis in environmental monitoring, defense, and industry, atmospheric flow tube mass spectrometry (AFT-MS) can fill a role that incorporates non-contact vapor analysis with the selectivity and low detection limits of mass spectrometry. AFT-MS has been applied to quantitating certain explosives by selective clustering with nitrate and more recently applied to detecting tributyl phosphate and dimethyl methylphosphonate as protonated species. Developing AFT-MS methods for organophosphorus species is appealing, given that this class of compounds includes a range of pollutants, chemical warfare agent (CWA) simulants, and CWA degradation products. A key aspect of targeting organophosphorus analytes has included the use of dopant ion chemistry to form adducts that impart additional analytical selectivity. The assessment of potential dopant molecules suited to enhance detection of these compounds is hindered by few published ion thermochemical properties for organophosphorus species, such as proton affinity, which can be used for approximating proton-bound dimer bond strength. As a preliminary investigation for the progression of sensing methods involving AFT-MS, we have applied both the extended kinetic method and computational approaches to eight organophosphorus CWA simulants to determine their respective gas-phase proton affinities. Notable observed trends, supported by computational efforts, include an increase in proton affinity as the alkyl chain lengths on the phosphonates increased. Graphical Abstract .

Chiral detection of entecavir stereoisomeric impurities through coordination with R-besivance and ZnII using mass spectrometry.

In this study, a mass spectrometry (MS)-based kinetic method (KM) is shown to be successful at analyzing a multichiral center drug stereoisomer, entecavir (ETV), both qualitatively and quantitatively. On the basis of the KM, the bivalent complex ion [MII (A)(ref*)2 ]2+ (MII  = divalent metal ion, A = analyte, and ref* = chiral reference) was set as precursor ion in MS/MS. The experiment results suggest strong chiral selectivity between ETV and its isomers when using ZnII coordinated with the chiral reference R-besivance (R-B). The logarithm of the fragment ion abundance ratio and the enantiomeric percentage (%) exhibits a strong linear relation because of the competitive loss of the reference and analyte. The product ion pair [ZnII (R-B)A-H]+ (m/z 733) and [ZnII (R-B)2 -H]+ (m/z 849), together with [R-B + H]+ (m/z 394) and [A + H]+ (m/z 278), can realize the identification of ETV and all of its chiral isomers. Theoretical calculation were also performed using the B3LYP functional with the 6-31G* and LanL2DZ basis set to clarify the mechanism of structural difference of these bivalent complex ions. The results reveal that MS-KM can be used to detect optical impurities without a chiral chromatographic column and fussy sample pretreatment. The established method has been used to determine stereoisomeric impurities of less than 0.1% in ETV crude drug, a demonstration of its simple and effective nature for rapid detection of stereoisomeric impurities.

A mathematical analysis to address the 6 degree-of-freedom segmental power imbalance.

Segmental power is used in human movement analyses to indicate the source and net rate of energy transfer between the rigid bodies of biomechanical models. Segmental power calculations are performed using segment endpoint dynamics (kinetic method). A theoretically equivalent method is to measure the rate of change in a segment's mechanical energy state (kinematic method). However, these two methods have not produced experimentally equivalent results for segments proximal to the foot, with the difference in methods deemed the "power imbalance." In a 6 degree-of-freedom model, segments move independently, resulting in relative segment endpoint displacement and non-equivalent segment endpoint velocities at a joint. In the kinetic method, a segment's distal end translational velocity may be defined either at the anatomical end of the segment or at the location of the joint center (defined here as the proximal end of the adjacent distal segment). Our mathematical derivations revealed the power imbalance between the kinetic method using the anatomical definition and the kinematic method can be explained by power due to relative segment endpoint displacement. In this study, we tested this analytical prediction through experimental gait data from nine healthy subjects walking at a typical speed. The average absolute segmental power imbalance was reduced from 0.023 to 0.046 W/kg using the anatomical definition to ≤0.001 W/kg using the joint center definition in the kinetic method (95.56-98.39% reduction). Power due to relative segment endpoint displacement in segmental power analyses is substantial and should be considered in analyzing energetic flow into and between segments.

Development of a rapid and inexpensive plasma glucose estimation by two-point kinetic method based on glucose oxidase-peroxidase enzymes.

A rapid and inexpensive plasma glucose estimation by two-point kinetic method based on glucose oxidase and peroxidase enzymes has been developed it takes only 11/2 minutes of time and validity of the method has been discussed.

Quantification of various APP-mRNA isoforms and epistasis in Lesch-Nyhan disease.

The present work is the development of a simple and specific kinetic method based on RT-PCR technique coupled with direct sequencing for quantification of various amyloid precursor protein-mRNA isoforms (APP-mRNA isoforms) in biological samples, especially for identifying the most abundant one that may decisive for the normal status or disease risk. Application of this kinetic method to the Lesch-Nyhan disease (LND) was performed and results indicated an epistasis between mutated hypoxanthine phosphoribosyltransferase1 (HPRT1) and APP genes. APP-mRNA isoform of 624bp, with a deletion starting after 49bp of the 5' end of exon 3 followed by a complete deletion of exons 4-15, mutations in exon 1: c.22C>T, p.L18F, and exon 3: c.269A>G, p.Q90R encoding APP207 isoform, was the most abundant one in most of the LND patients and would be responsible for the neurobehavioral syndrome in these patients. The method is useful for identifying the defective APP-mRNA isoform in LND patients, and in neurodevelopmental and neurodegenerative disorders in which the APP gene is involved in the pathogenesis of diseases such as autism, fragile X syndrome, amyotrophic lateral sclerosis, and Alzheimer's disease, and may pave the way for new strategies applicable to rational antisense drugs design.

A neurodevelopmental disorder with a nonsense mutation in the Ox-2 antigen domain of the amyloid precursor protein (APP) gene.

We report a patient, an infant with a neurodevelopmental disorder manifesting intractable complex partial epilepsy, bull's eye maculopathy, microcephaly, bilateral cataracts, truncal hypotonia, and spasticity of all four extremities. Sequencing of genomic DNA revealed mutations in (a) exon 8 (Ox-2 antigen domain) of the amyloid precursor protein (APP) gene: c.1075C>T, p.Arg359* (b) exon 8 of the senataxin (SETX) gene: c.4738C>T, p.Arg1580Cys, and (c) exon 2 of the ceroid-lipofuscinosis, neuronal 8 (CLN8) gene: c.685C>G, p.Pro229Ala. Using a quantitative method for measurement of various APP-mRNA isoforms, we found that the APP-mRNA isoform of 624 bp with a deletion starting after 49 bp of the 5' end of exon 3 followed by a complete deletion of exons 4-15, mutations in exon 1: c.22C>T, p.L18F, and exon 3: c.269A>G, p.Q90R encoding APP207 isoform was the most abundant one, and would appear to be responsible for the clinical manifestations. This is the first example that may underline the role of the epigenetic regulation in the expression of APP gene leading to a neurodevelopmental disorder resulting from a nonsense mutation in the Ox-2 antigen domain.

Establishment of kinetic detection method for PKA content / 中国输血杂志

【Objective】 To develop and verify a kinetic method for the determination of prekallikrein activator (PKA) content. 【Methods】 The optimal reaction conditions were determined by comparing the factors of pH and ionic strength of different sample dilution buffers, incubation time of each procedure, and incubation temperature. The accuracy, specificity, precision, linearity, stability and durability of the method were validated. 【Results】 The sample was diluted with 0.05 mol/L Tris-HCl buffer (pH8.5, containing 0.15 mol/L NaCl) and incubated by prekallikrein (PK) at 37℃ for 20 min. After that, the substrate S-2302 was added. Within 10 min before the measurement, the absorbance change rate reached △A405/min. The validation results indicated that the linear range of the method was (0.5~4.0)IU/mL, while the recovery of calibration standard was 96.9%~103.7% with the R2 value more than 0.99. The specificity test showed that human serum albumin, excipients of intravenous human immunoglobulin (pH4), low pH and protein content had no significant effect on the detection of PKA, The recovery rates of standard sample solution in the specificity experiment were 98.0% (0.9% sodium chloride solution), 95.3% (0.46% sodium caprylate solution), 96.7% (10% maltose solution, pH4.0), 94.0%(20%BSA), and 94.0%(5%BSA, pH4.0), respectively. The accuracy and precision of the method can meet requirements in the range between 0.5 and 4.0 IU/mL. The inter-batch recovery rate of quality control samples were between 96.4%~109.5% with the coefficients of variation(CV) between 0.2%~6.9%, while the intra-batch recovery rate were between 101.5%~102.9% with the CV between 2.6%~5.9%. The linearity, accuracy and precision of the assay can meet the requirements when PK and S-2302 were placed at room temperature for less than 6 hours, with the recovery rate of quality control samples between 94.9%~109.9%. The end-point method and kinetic method were used to determine the PKA in 20 batches of human serum albumin, and the consistency showed that there was no significant difference between the two methods(P>0.05). 【Conclusion】 A kinetic method for determination of PKA content with good linearity, specificity, accuracy, precision, stability and durability has been established. Compared with the method in ChP, the new method is more convenient, accurate and rapid to determine the content of PKA in human albumin and human immunoglobulin (pH4) for intravenous injection.

Vitamin C: an experimental and theoretical study on the gas-phase structure and ion energetics of protonated ascorbic acid.

In order to investigate the gas-phase mechanisms of the acid catalyzed degradation of ascorbic acid (AA) to furan, we undertook a mass spectrometric (ESI/TQ/MS) and theoretical investigation at the B3LYP/6-31 + G(d,p) level of theory. The gaseous reactant species, the protonated AA, [C6 H8 O6 ]H+ , were generated by electrospray ionization of a 10-3 M H2 O/CH3 OH (1 : 1) AA solution. In order to structurally characterize the gaseous [C6 H8 O6 ]H+ ionic reactants, we estimated the proton affinity and the gas-phase basicity of AA by the extended Cooks's kinetic method and by computational methods at the B3LYP/6-31 + G(d,p) level of theory. As expected, computational results identify the carbonyl oxygen atom (O2) of AA as the preferred protonation site. From the experimental proton affinity of 875.0 ± 12 kJ mol-1 and protonation entropy ΔSp 108.9 ± 2 J mol-1 K-1 , a gas-phase basicity value of AA of 842.5 ± 12 kJ mol-1 at 298 K was obtained, which is in agreement with the value issuing from quantum mechanical computations. Copyright © 2016 John Wiley & Sons, Ltd.