C vs N: which end of the cyanide anion is a better hydrogen bond acceptor?
J Phys Chem A
; 118(35): 7418-23, 2014 Sep 04.
Article
em En
| MEDLINE
| ID: mdl-24707902
ABSTRACT
The ability of the C and N ends of the cyanide anion (CN(-)) as acceptors of hydrogen bonds, an experimentally difficult problem, has been computationally examined in this study. Structures obtained in our previous work involving cyanide binding within the cavity of a triazolophane macrocycle (Chem.-Eur. J. 2011, 17, 9123-9129) were used to analyze the problem. Three different approaches involving (a) breakdown of the triazolophane into smaller components, (b) population analyses, and (c) ion-dipole analyses helped demonstrate that the N terminus of cyanide is a slightly better hydrogen bond acceptor than the C terminus even though it is not the site of protonation or covalent bond formation. This outcome reflects a competition between the preference for noncovalent interactions at the nitrogen and covalent bond formation at the carbon.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Cianetos
/
Ânions
Idioma:
En
Revista:
J Phys Chem A
Ano de publicação:
2014
Tipo de documento:
Article