This paper constitutes the fifth part of a general review of the gas‐phase protonation thermochemistry of polyfunctional molecules (Part 1: Theory and methods, Mass Spectrom Rev 2007, 26:775–835, Part 2: Saturated basic sites, Mass Spectrom Rev 2012, 31:353–390, Part 3: Amino acids, Mass Spectrom Rev 2012, 31:391–435, Part 4: Carbonyl as basic site, Mass Spectrom Rev 2015, 34:493–534). This part is devoted to non‐aromatic molecules characterized by a lone pair located on a sp² nitrogen atom, it embraces functional groups such as imines, amidines, guanidines, diazenes, hydrazines, oximes, and phosphazenes. Specific examples are examined under five major chapters. In the first one, aliphatic and unsaturated (conjugated and cyclic) imines, hydrazones, and oximes are considered. A second chapter describes the protonation energetic of aliphatic, conjugated, or cyclic amidines. Guanidines, polyguanides, and biomolecules containing guanidine were examined in the third chapter. A fourth chapter describes the particular case of the phosphazene molecules. Finally, diazenes and azides were considered in the last chapter. Experimental data were re‐evaluated according to the presently adopted basicity scale, i.e., PA(NH₃) = 853.6 kJ/mol, GB (NH₃) = 819 kJ/mol. Structural and energetic information given by G4MP2 quantum chemistry computations on typical systems are presented. © 2016 Wiley Periodicals, Inc. Mass Spec Rev 37:139–170, 2018

中文翻译：

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多官能分子的气相碱性。第5部分：非芳香族sp2含氮化合物

本文构成了多官能分子气相质子热化学概述的第五部分（第1部分：理论和方法，Mass Spectrom Rev 2007，26：775-835，第2部分：饱和碱性位点，Mass Spectrom Rev 2012 ，31：353–390，第3部分：氨基酸，质谱修订版2012，31：391–435，第4部分：以羰基为基本位点，质谱修订版2015，34：493–534）。此部分致力于非芳香族分子，其特征是位于sp ²上的孤对氮原子，它包含亚胺，am，胍，二氮烯，肼，肟和磷腈等官能团。具体示例在五个主要章节中进行了探讨。在第一个中，考虑了脂族和不饱和（共轭和环状）亚胺，和肟。第二章介绍脂族，共轭或环状am的质子化能。第三章对胍，聚胍和含有胍的生物分子进行了研究。第四章介绍了磷腈分子的特殊情况。最后，在上一章中考虑了二叠氮和叠氮化物。根据目前采用的碱度等级重新评估了实验数据，即PA（NH ₃）= 853.6 kJ / mol，GB（NH ₃）= 819 kJ / mol。给出了由G4MP2量子化学计算在典型系统上给出的结构和能量信息。©2016 Wiley Periodicals，Inc.质谱修订版37：139–170，2018