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The halogen bond was compared with the hydrogen bond in an equivalent series based on succinimide. The halogen\u2010bond energies are in the range \u221260 to \u221220\u2005kJ\u2009mol<jats:sup>\u22121<\/jats:sup> and change regularly with pyridine basicity and the Lewis acidity of the halogen. The halogen\u2010bond energies correlate linearly with the product of charges on the contact atoms, which indicates a predominantly electrostatic interaction. The binding enthalpies in solution are around 19\u2005kJ\u2009mol<jats:sup>\u22121<\/jats:sup> less negative due to solvation effects. The optimised geometries of the complexes in the gas phase are comparable to those of the solid\u2010state structures, and the effects of the supramolecular surroundings in the latter are discussed. The bond energies for the hydrogen\u2010bonded series are intermediate between the halogen\u2010bond energies of iodine and bromine, although there are specific differences in the geometries of the halogen\u2010 and hydrogen\u2010bonded complexes.<\/jats:p>","DOI":"10.1002\/chem.201605686","type":"journal-article","created":{"date-parts":[[2017,1,23]],"date-time":"2017-01-23T04:47:05Z","timestamp":1485146825000},"page":"5244-5257","source":"Crossref","is-referenced-by-count":90,"title":["Halogen and Hydrogen Bonding between (<i>N<\/i>\u2010Halogeno)\u2010succinimides and Pyridine Derivatives in Solution, the Solid State and In Silico"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4383-5898","authenticated-orcid":false,"given":"Vladimir","family":"Stilinovi\u0107","sequence":"first","affiliation":[{"name":"Department of Chemistry Faculty of Science, University of Zagreb  Horvatovac 102a Zagreb 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