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• W2138845770 abstract "Abstract The gas‐phase basicities (GBs) for a representative set of six formamidine ureas with variations in the imino substituent [RN=CH–N(Me)C(O)NMe 2 ] were determined in proton‐transfer equilibria by ion cyclotron resonance (ICR) mass spectrometry and further explored with calculations at the B3LYP/6‐31+G* level. The GB values, ranging from 218.6 to 230.9 kcal mol –1 , were also compared with those previously reported for N 1 , N 1 ‐dimethyl‐ N 2 ‐substituted formamidines. For all compounds investigated, protonation occurs preferentially at the imino nitrogen. In the cases of R = n ‐C 7 H 15 , Ph(CH 2 ) 3 and Ph, no stable O ‐protonated structures exist which can transfer proton to the N atom without a significant barrier. Relative GBs were linearly correlated to the inductive effect of the imine nitrogen substituents. The calculated structures are also given, and the calculated basicities are in good agreement with the observed values. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)" @default.
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• W2138845770 date "2005-12-14" @default.
• W2138845770 modified "2023-09-27" @default.
• W2138845770 title "Substituent Effects on the Gas‐Phase Basicity of Formamidine Ureas" @default.
• W2138845770 cites W1582796594 @default.
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• W2138845770 doi "https://doi.org/10.1002/ejoc.200500516" @default.
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