Effect of strain on gas‐phase basicity of (E)‐1‐methyl‐2‐(1‐methyl‐2‐adamantylidene)adamantane. (27th March 2015)

• Record Type: Journal Article
• Authors: Kekišev, Ott; Kaljurand, Ivari; Toom, Lauri; Lenoir, Dieter; Burk, Peeter; Järv, Jaak
• Is Part Of: Journal of physical organic chemistry. Volume 28:Number 7(2015:Jul.)
• Page Start: 447
• Page End: 451
• Publication Date: 2015-03-27
• Subjects: Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3435
• Languages: English
• ISSNs: 0894-3230

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Steric strain, caused by forced deformation of double bond geometry, has significant impact on alkene reactivity, as was shown by a study of the gas‐phase basicity of (<italic>E</italic>)‐1‐methyl‐2‐(1‐methyl‐2‐adamantylidene)adamantane. The Gibbs free energy of the strain effect in this compound was 42 kJ/mol. This analysis was made based on adamantylideneadamantane as a congeneric reference compound with a planar double bond. It was concluded that gas‐phase basicity could serve as a valuable alternative indicator for quantification of steric strain in alkenes. Copyright © 2015 John Wiley &amp; Sons, Ltd.</p> </abstract>