Some Intrinsic Features of Hydroxylamines, Oximes and Hydroxamic Acids: Integration of Theory and Experiment

1 Introduction 2 Analysis of Covalent and Noncovalent Interactions 3 Computational Approach 4 Lone Pair–Lone Pair Repulsion 5 Comparison of Prototypical Examples 6 Oxime Isomerism 7 Hydrogen Bonding 8 Acidity/Basicity 9 Global and Local Polarizability 10 Conclusion 11 Acknowledgment Keywords: intrinsic features of hydroxylamines, oximes and hydroxamic acids-theory and experiment; covalent and noncovalent interaction analysis; ionization energy; surface electrostatic potential, and its most positive and most negative values; lone pair–lone pair repulsion; computational approach; hydroxylamines, oximes and hydroxamic acids-with adjacent nitrogen and oxygen atoms; oxime isomerism