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Isotope effect studies on elimination reactions. III. nitrogen isotope effects in the E2 reaction of ethyltrimethylammonium and 2-phenlylethyltrimethylammonium ions

Journal Article · · Canadian Journal of Chemistry (Canada)
DOI:https://doi.org/10.1139/v63-253· OSTI ID:4686097

Nitrogen isotope effects were determined for the E2 reaction of two quaternary ammonium salts with ethoxide ion in ethanol. Ethyltrimethylammonium iodide gave k14k15 values of 1.017 at 60° and 1.015 at 95°, while 2-phenylethyltrimethylammonium bromide gave 1.013 at 46 deg and 1.609 at 60 deg . These results and the BETA -deuterium isotope effects reported by others were interpreted in terms of the relative extent of CαN+ and Cβ--H bond weakening in the transition states of the two reactions.

Research Organization:
McMaster Univ., Hamilton, Ont.
Sponsoring Organization:
USDOE
NSA Number:
NSA-17-028925
OSTI ID:
4686097
Journal Information:
Canadian Journal of Chemistry (Canada), Journal Name: Canadian Journal of Chemistry (Canada) Vol. Vol: 41; ISSN CJCHA
Country of Publication:
Country unknown/Code not available
Language:
English