Title
Chloromethyl phenyl ether in the gas phase, studied by electron diffraction, infrared and ab-initio calculations Chloromethyl phenyl ether in the gas phase, studied by electron diffraction, infrared and ab-initio calculations
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Amsterdam ,
Subject
Chemistry
Source (journal)
Journal of molecular structure. - Amsterdam
Volume/pages
344(1995) :1/2 , p. 117-126
ISSN
0022-2860
ISI
A1995QC03800014
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
The molecular structure of chloromethyl phenyl ether (CMPE) is investigated from gas phase electron diffraction data and IR frequencies in CS2 solution, complemented with geometry relaxed ab initio calculations on the HF/4-21C/3-3-31G level. The anomeric effect greatly affects the geometrical parameters, among other things making the C(sp(3))-O bond shorter than the C(sp(2))-O bond, Furthermore, the anomeric interaction significantly shifts the equilibrium between an e rotameric form (OC(sp(3)) in-plane with phenyl ring) and an o rotameric (OC(sp(3)) approximately perpendicular to phenyl ring) towards the o form. In fact CMPE appears as a mixture of about equal amounts of (e, sc) and (o, sc) conformations. The IR spectral frequencies are reassigned and analogous geometrical trends with anisole rotamers are discussed.
E-info
https://repository.uantwerpen.be/docman/iruaauth/21cb1d/9364278.pdf
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