Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/5109
Title: Conformational study of erythritol and threitol in the gas state by density functional theory calculations
Authors: Jesus, António J. Lopes 
Tomé, Luciana I. N. 
Rosado, Mário Túlio S. 
Leitão, M. Luísa P. 
Redinha, José S. 
Keywords: Erythritol; Threitol; Conformation; Intramolecular H-bonds; Enthalpy; Gibbs energy
Issue Date: 2005
Citation: Carbohydrate Research. 340:2 (2005) 283-291
Abstract: Density functional theory calculations using the B3LYP functional and the 6-311++G(d,p) basis set were carried out on the isolated molecules of erythritol and L-threitol. For the meso isomer, a relatively large number of conformers have to be considered to describe the gas state structure. The lowest energy conformer is characterized by the establishment of a strong intramolecular H-bond between the two terminal hydroxyl groups, giving rise to a seven-membered ring and two additional weaker H-bonds between vicinal OH groups. In the case of L-threitol, two conformers are predominant in the gas state, and both are stabilized by the formation of a cyclic system of four intramolecular hydrogen bonds involving all OH groups. The conformational stability in both diastereomers is discussed in terms of the electronic energy and of the Gibbs energy. The weighted mean enthalpy of both diastereomers in the gas state at 298.15 K was obtained from the thermodynamic data and Boltzmann populations of the low-energy conformers.
URI: http://hdl.handle.net/10316/5109
DOI: 10.1016/j.carres.2004.11.018
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

Files in This Item:
File Description SizeFormat
file7bcadad1adaa4649b8f06570f9f5058c.pdf233.25 kBAdobe PDFView/Open
Show full item record

WEB OF SCIENCETM
Citations 50

9
checked on Jan 2, 2021

Page view(s)

315
checked on Jan 21, 2021

Download(s)

133
checked on Jan 21, 2021

Google ScholarTM

Check

Altmetric

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.