Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH2CH3, in the solid phase and NBO analysis.
Acta Crystallogr B
; 67(Pt 4): 350-6, 2011 Aug.
Article
em En
| MEDLINE
| ID: mdl-21775813
ABSTRACT
The molecular structure of ethyl chlorothioformate, ClC(O)SCH(2)CH(3), has been investigated in the solid phase by X-ray diffraction analysis at low temperature using a miniature zone-melting procedure and IR laser radiation. The crystalline solid consists exclusively of molecules with the synperiplanar conformation with respect to the C=O double bond and the S-C single bond, and gauche orientation of the ethyl group (syn-gauche). These results coincide with previous studies devoted to gas-phase conformational properties. The conformational preference for the ClC(O)SY (Y = Cl, CF(3), CH(3) and CH(2)CH(3)) series of molecules was rationalized using the natural bond orbital (NBO) scheme. It was found that both resonance (mesomeric) and anomeric (hyperconjugation) intermolecular charge-transfer interactions are important for describing the syn â anti equilibrium, also illustrating the effect of electronegativity of the substituent in the conformation preference of the ClC(O)S- moiety. On the basis of the atoms in molecules (AIM) theory, intermolecular interactions have been characterized in the B3LYP/6-31G** periodic boundary electron density.
Texto completo:
1
Base de dados:
MEDLINE
Idioma:
En
Revista:
Acta Crystallogr B
Ano de publicação:
2011
Tipo de documento:
Article
País de afiliação:
Argentina