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Proton affinities by reactant ion monitoring: Triphenyl group Va compounds
Author(s) -
Tran Vinh Thi,
Munson Burnaby
Publication year - 1986
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.1210210109
Subject(s) - affinities , chemistry , substituent , proton affinity , proton , ion , ring (chemistry) , alkyl , hydrogen , group (periodic table) , medicinal chemistry , stereochemistry , protonation , organic chemistry , physics , quantum mechanics
Proton affinities of a series of triphenyl Group Va compounds have been determined by bracketing using reactant ion monitoring: (C 6 H 5 ) 3 N = 904 ± 8 kJ mol −1 , (C 6 H 5 ) 3 P = 968 ± 5 kJ mol −1 , (C 6 H 5 ) 3 As = 904 ± 8 kJ mol −1 and (C 6 H 5 ) 3 Sb = 846 ± 8 kJ mol −1 . The large difference in substituent effect of phenyl for hydrogen between As or P and N may result from overlap of the 2p orbitals of N with the sp 2 orbitals on the ring carbons and lack of overlap for P or As. Proton affinities of phenylalkylphosphine oxides are essentially the same, 904 ± 8 kJ mol −1 , independent of alkyl group.