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The Gas‐Phase Acidity of HCP, CH 3 CP, HCAs, and CH 3 CAs: An Unexpected Enhanced Acidity of the Methyl Group
Author(s) -
Mó Otilia,
Yáñez Manuel,
Guillemin JeanClaude,
Riague El Hassan,
Gal JeanFrançois,
Maria PierreCharles,
Dubin Poliart Christine
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20021104)8:21<4919::aid-chem4919>3.0.co;2-j
Subject(s) - chemistry , deprotonation , gas phase , fourier transform ion cyclotron resonance , nitrogen , analytical chemistry (journal) , methyl group , mass spectrometry , ion , medicinal chemistry , inorganic chemistry , group (periodic table) , organic chemistry , chromatography
The gas‐phase acidities of methylidynephosphine, HCP, ethylidynephosphine, CH 3 CP, and ethylidynearsine, CH 3 CAs, have been measured by means of Fourier Transform Ion Cyclotron Resonance (FTICR) mass spectrometry and calculated at the CCSD(T)/6‐311+G(3df,2p)//QCISD/ 6‐311+G(df,p) level of theory. An analysis of these results shows that, in contrast to the well‐known fact that HCN is a stronger acid than CH 3 CN, CH 3 CP and CH 3 CAs are more acidic than HCP and HCAs, respectively. The most important consequence of this unexpected effect is that while HCP and HCAs are found to be weaker acids than HCN, the opposite trend is found for the corresponding methyl derivatives, the acidity of which increases as CH 3 CN