Exploring the non-covalent interactions behind the formation of amine–water complexes: The case of the N-allylmethylamine monohydrate

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dc.contributor.authorSilva, Weslley G. D. P.
dc.contributor.authorPoonia, Tamanna
dc.contributor.authorvan Wijngaarden, Jennifer
dc.date.accessioned2021-12-14T21:48:27Z
dc.date.available2021-12-14T21:48:27Z
dc.date.issued2021-03-18
dc.date.submitted2021-10-26T19:17:12Zen_US
dc.description.abstractThe conformational landscape of the monohydrated complex of N-allylmethylamine (AMA–w) was investigated for the first time using rotational spectroscopy from 8–20 GHz and quantum chemistry calculations. From a total of nine possible energy minima within 10 kJ mol-1, transitions for the two most stable conformers of AMA–w were detected, and assigned aided by DFT and ab initio MP2 predictions. The observed rotational transitions displayed characteristic hyperfine splittings due to the presence of the 14N quadrupolar nucleus. Quantum theory of atoms in molecules (QTAIM), non-covalent interaction (NCI) and natural bond orbital (NBO) analyses showed that the observed conformers of AMA–w are stabilized by two intermolecular interactions consisting of a dominant N…H–O and a secondary C–H…O hydrogen bond (HB) in which the water molecule acts simultaneously as a HB donor and acceptor. The HBs formed with water do not change the relative energy ordering of the most stable conformers of AMA but do affect the stability of higher energy conformations by disrupting the intramolecular forces responsible for their geometries. By comparing the intermolecular interaction energies with those of the monohydrates of the simplest primary (methylamine, MA), secondary (dimethylamine, DMA) and tertiary (trimethylamine, TMA) amines using symmetry-adapted perturbation theory (SAPT) calculations, we find that AMA forms the strongest bound complex with water. This is rationalized through the identification of subtle differences in stabilizing and destabilizing contributions across the amine–w series of complexes.en_US
dc.description.sponsorshipNSERC RGPIN/0653-2016en_US
dc.identifier.citationSilva, W. G. D. P.; Poonia, T.; van Wijngaarden, J. Phys. Chem. Chem. Phys. 2021, 23, 7368-7375en_US
dc.identifier.doi10.1039/D1CP00420D
dc.identifier.urihttp://hdl.handle.net/1993/36135
dc.language.isoengen_US
dc.publisherPhysical Chemistry Chemical Physicsen_US
dc.rightsopen accessen_US
dc.subjectmicrowave spectroscopyen_US
dc.subjectquantum chemistry calculationsen_US
dc.subjectnon-covalent interactionsen_US
dc.subjectmicrosolvationen_US
dc.subjectaminesen_US
dc.titleExploring the non-covalent interactions behind the formation of amine–water complexes: The case of the N-allylmethylamine monohydrateen_US
dc.typePreprinten_US
local.author.affiliationFaculty of Scienceen_US
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