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The substituent effect in the fragmentation of phenylcyclohexanols
Author(s) -
De Angelis F.,
Forcellese M. L.,
Gambacorta A.,
Nicoletti R.
Publication year - 1977
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210120512
Subject(s) - substituent , fragmentation (computing) , chemistry , ion , cyclohexanol , ionic bonding , polar effect , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry , catalysis , computer science , operating system
All the main fragmentation pathways undergone by trans ‐4‐ and trans ‐2‐ p ‐substituted phenylcyclohexanols have been studied, and the ionic abundances have been correlated with the σ constants. This analysis shows that electron withdrawing substituents, increasing the fraction of molecular ions having sufficient energy to decompose, favour all fragmentations. However, along with this ‘non‐specific’ substituent effect, there is a ‘specific’ effect, in the opposite sense, increasing the formation of the [M—59] + and [M—85] + ions with increasing electron releasing power of the substituents. The loss of water, although it is almost exclusively a 1,4 elimination in the case of trans phenyl cyclohexanols, is not specifically influenced by the substituents.