150 years later: a look at Loschmidt's contributions to organic chemistry1. (13th February 2013)

• Record Type: Journal Article
• Authors: Roth, Heinz D.
• Is Part Of: Journal of physical organic chemistry. Volume 26:Number 9(2013:Sep.)
• Page Start: 755
• Page End: 763
• Publication Date: 2013-02-13
• Subjects: Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3089
• Languages: English
• ISSNs: 0894-3230

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Examining the structures presented by Loschmidt in 1861 shows that he portrayed organic structures in a visually appealing way, but the structures do not support several claims and accolades of Loschmidt's modern‐day champions. There is serious doubt that Loschmidt viewed benzene as a planar cyclic array of six carbon atoms; he did not understand positional isomerism of benzene derivatives or the essence of geometric isomerism. He did not recognize that carbons of the C₆ nucleus could only be singly bonded to a substituent. Concerning his "prediction" of cyclopropane, Loschmidt may have been the first to consider a "circular" array of three atoms; this achievement must be viewed in the light of similar predictions for a cyclic dinitrogen oxide, tetracyclohexane, heptacyclononane, and a [1, 1]‐metacyclophane. His structures worked well for strings of sp²‐hybridized carbons or for molecules with chains of tri‐substituted carbons. Loschmidt did not differentiate between the bond lengths of double and triple bonds, as claimed. Copyright © 2013 John Wiley &amp; Sons, Ltd.</p> </abstract>