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Experimental and Theoretical Charge Density Study of the Neurotransmitter Taurine
Author(s) -
Hibbs David E.,
AustinWoods Charles J.,
Platts James A.,
Overgaard Jacob,
Turner Peter
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390100
Subject(s) - delocalized electron , taurine , monoclinic crystal system , charge density , zwitterion , crystal (programming language) , hydrogen bond , electron density , chemistry , crystallography , crystal structure , moiety , density functional theory , materials science , computational chemistry , electron , stereochemistry , molecule , amino acid , physics , organic chemistry , biochemistry , quantum mechanics , computer science , programming language
The experimental electron density distribution in taurine, 2‐aminoethane sulfonic acid, 1 , has been determined from high‐resolution X‐ray diffraction data collected at a temperature of 100 K. Taurine crystallizes as a zwitterion in the monoclinic space group P 2 1 / c. Topological analysis of the experimental electron density and a comparison with high‐level theoretical gas‐phase calculations show that the crystal environment has a significant influence on the electronic configuration of the sulfonate moiety in 1 , which in the crystal is more delocalized than in the gas phase. This crystal effect is mainly due to hydrogen bonding.