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Effects of solvents on the tautomerization of N,N‐ dimethylglycine
Author(s) -
Headley Allan D.,
Corona Rita E.,
Cheung Eric T.
Publication year - 1997
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(199712)10:12<898::aid-poc959>3.0.co;2-k
Subject(s) - zwitterion , chemistry , tautomer , solvation , intramolecular force , solvent , carboxylate , hydrogen bond , solvent effects , conformational isomerism , polarizability , computational chemistry , polarizable continuum model , medicinal chemistry , organic chemistry , molecule
The effects that solvents have on the tautomerization of N,N ‐dimethylglycine are analyzed and the solvent's dipolarity/polarizability and acidic properties appear to play important roles in the solvation of the zwitterionic tautomer. Owing to the existence of a stable intramolecular hydrogen‐bonded conformer of the zwitterion, in which the acidic hydrogen of the ion is hydrogen bonded to the carboxylate functionality, solvation of the zwitterion by basic solvents is not very important. © 1997 John Wiley & Sons, Ltd.