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Conformational analysis of 2‐cyano‐1,1‐dihydroxyethane in solution
Author(s) -
Aviyente Viktorya,
Varnali Tereza,
RuizLópez Manuel F.
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199602)9:2<119::aid-poc760>3.0.co;2-k
Subject(s) - chemistry , anomeric effect , ab initio , computational chemistry , anomer , polar , molecule , solvent polarity , solvent effects , ethylene , solvent , polarity (international relations) , gas phase , stereochemistry , organic chemistry , biochemistry , physics , astronomy , cell , catalysis
The conformational space of the 2‐cyano‐1,1‐dihydroxyethane molecule was studied at the semi‐empirical PM3 level and ab initio MP2/6‐31G**//6‐31G level in the gas phase and in a low‐polarity medium. This system has been chosen as a model compound for 2‐cyanocyclohexanone propylene and ethylene acetals. This has allowed the study of the role of polar groups on the relative conformation of two adjacent OH groups, which is of interest also in relation to the anomeric effect in carbohydrate chemistry. Solvent effects are taken into account using a continuum model with general cavity shapes.