TAUTOMERISM OF HISTAMINE REVISITED

Citation
G. Karpinska et al., TAUTOMERISM OF HISTAMINE REVISITED, Journal of molecular structure. Theochem, 369, 1996, pp. 137-144
Citations number
26
Categorie Soggetti
Chemistry Physical
ISSN journal
01661280
Volume
369
Year of publication
1996
Pages
137 - 144
Database
ISI
SICI code
0166-1280(1996)369:<137:TOHR>2.0.ZU;2-R
Abstract
The tautomerism of the histamine molecule was explored based on quantu m chemical calculations both in the gaseous state and in aqueous mediu m. Structural optimizations were performed at the ab initio Hartree-Fo ck (HF) and the second order Moller-Plesset (MP2) perturbation level. The most stable tautomer in aqueous medium appeared to be the N(3)-H m onocation; with strong intramolecular hydrogen bonding. Results from c alculations prove that the previous hypothesis on interaction with the hypothetical H-2 receptor remains valid, even though this hypothesis involved a slightly different assumption regarding the structure of th e most stable form. The most stable neutral form in aqueous medium tur ned out to be the opened N(3)-H gauche structure.