Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/17764
Title: FTIR studies of hydrogen bonding between α,β-unsaturated esters and alcohols
Authors: Tonge, P.J. 
Fausto, R. 
Carey, P.R. 
Issue Date: 15-Jun-1996
Publisher: Elsevier
Serial title, monograph or event: Journal of Molecular Structure
Volume: 379
Abstract: The enthalpy (and entropy) of hydrogen bond formation has been measured between the ester carbonyl groups of the two α,β-unsaturated esters thienylacryloyl (TAOMe) and 5-methylthienylacryloyl (5MeTAOMe) methyl ester and the hydrogen bond donors ethanol, phenol and 3,5-dichlorophenol in CCl4. For the esters, the hydrogen bonding strengths were measured by quantitating the amount of bound and unbound donor, using the OH stretching region, as a function of temperature and applying the van't Hoff equation. The decrease in νCO of the ester carbonyl group upon hydrogen bond formation ΔνCO has also been measured and correlated with the enthalpy of hydrogen bond formation. A linear correlation is observed between the enthalpy of hydrogen bond formation −ΔH and ΔνCO, with −ΔH = 1.36ΔνCO − 16.1, where ΔH is measured in kJ mol−1 and Δν in cm−1. Comparison with data for other carbonyl acceptor compounds indicates that the carbonyl group of the above α,β-unsaturated esters is more readily polarized than the carbonyl group of saturated esters or ketones. The quantitative relationship between −ΔH and ΔνCO derived here has been used to determine the change in the enthalpy of hydrogen bond formation between substrate and enzyme groups in a series of acylserine proteases.
URI: http://hdl.handle.net/10316/17764
DOI: 10.1016/0022-2860(95)09117-3
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

Files in This Item:
File Description SizeFormat
Journal of Molecular Structure, 379 (1996) 135.pdf620.75 kBAdobe PDFView/Open
Show full item record

SCOPUSTM   
Citations

29
checked on Jun 25, 2019

WEB OF SCIENCETM
Citations

27
checked on Jun 25, 2019

Page view(s)

221
checked on Oct 15, 2019

Download(s)

76
checked on Oct 15, 2019

Google ScholarTM

Check

Altmetric

Dimensions


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