Linked Life Data

20491502

Source:http://linkedlifedata.com/resource/pubmed/id/20491502

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
12
pubmed:dateCreated
2010-6-11
pubmed:abstractText
The thermodynamics of the O-H...B hydrogen bond (HB) has been determined in CCl(4) by FTIR spectrometry for a wide variety of carbon pi bases, oxygen bases, and miscellaneous first- to fourth-row bases, using 4-fluorophenol as a reference hydrogen-bond donor (HBD). After inclusion of previously studied nitrogen, sulfur, and halogen bases, this 4-fluorophenol affinity scale contains 314 varied organic bases and ranges over 40 kJ mol(-1). The 4-fluorophenol affinity scale in CCl(4) is shown to be applicable to most HBDs in most media, provided a small family dependence is taken into account. The HB affinity orders are quantitatively established according to the atomic acceptor site or to its bearing functional group. A comprehensive survey of the influence of substituents on these affinity orders is then achieved, considering electronic and steric effects, as well as effects of vinylogy or iminology. Iminology is found to be more efficient than vinylogy for transmitting resonance effects. Steric effects are shown to be less important in HB affinity than in HB basicity since they mainly act on the HB entropy. The spatial proximity of two acceptor sites can favor complexation through three-center hydrogen bonds, leading to superhydrogen-bond bases on the affinity scale.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
Jun
pubmed:issn
1520-6904
pubmed:author
pubmed:issnType
Electronic
pubmed:day
18
pubmed:volume
75
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
4105-23
pubmed:year
2010
pubmed:articleTitle
An enthalpic scale of hydrogen-bond basicity. 4. Carbon pi bases, oxygen bases, and miscellaneous second-row, third-row, and fourth-row bases and a survey of the 4-fluorophenol affinity scale.
pubmed:affiliation
Laboratoire CEISAM, UMR CNRS 6230, Faculté des Sciences et des Techniques, Université de Nantes, 2, rue de la Houssinière, BP 92208, 44322 Nantes, Cedex 3, France. christian.laurence@univ-nantes.fr
pubmed:publicationType
Journal Article