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dc.contributor.authorHelttunen, Kaisa
dc.contributor.authorLehtovaara, Lauri
dc.contributor.authorHäkkinen, Hannu
dc.contributor.authorNissinen, Maija
dc.date.accessioned2018-10-29T09:57:36Z
dc.date.available2018-10-29T09:57:36Z
dc.date.issued2013
dc.identifier.citationHelttunen, K., Lehtovaara, L., Häkkinen, H., & Nissinen, M. (2013). Crystal Structures and Density Functional Theory Calculations of o-and p-Nitroaniline Derivatives: Combined Effect of Hydrogen Bonding and aromatic interactions on dimerization energy. <i>Crystal Growth and Design</i>, <i>13</i>(8), 3603-3612. <a href="https://doi.org/10.1021/cg4005714" target="_blank">https://doi.org/10.1021/cg4005714</a>
dc.identifier.otherCONVID_22969614
dc.identifier.otherTUTKAID_58907
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/59984
dc.description.abstractThe interplay of strong and weak hydrogen bonds, dipole–dipole interactions, and aromatic interactions of o- and p-nitroaniline derivatives was studied by combining crystal structure analysis and density functional theory (DFT) calculations. Crystal structures of four 2-nitroaniline derivatives, 2-((2-nitrophenyl)amino)ethyl methanesulfonate (1A), 2-((2-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (2A), N,N′-((1,3-phenylenebis(oxy))bis(ethane-2,1-diyl))bis(2-nitroaniline) (3A), and N-(2-chloroethyl)-2-nitroaniline (4A), and crystal structures of three 4-nitroaniline derivatives, 2-((4-nitrophenyl)amino)ethyl methanesulfonate (1B), 2-((4-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (2B), and tert-butyl-(2-((4-nitrophenyl)amino)ethyl) carbonate (5B), were analyzed with regard to intra- and intermolecular hydrogen bonding and π–π interactions. The effect of o/p-substitution on π-electron distribution, aromaticity of the nitroaniline ring, and relative strength of intra- and intermolecular weak interactions were compared using HOMA indices, Hirshfeld surfaces, and DFT calculations. The 2-nitroaniline derivatives contain an intramolecular hydrogen bond between amino and nitro groups, creating a six-membered chelate ring, which formed pseudostacked structures with aromatic rings. van der Waals corrected DFT calculations showed that stacking of a phenyl and a chelate ring contributed significantly to the dimerization of 1A and 2A. Therefore, it can be concluded that the phenyl–chelate interactions are an important factor in stacking of the monomers in addition to C–H···O hydrogen bonding. In 4-nitroaniline derivatives, intermolecular N–H···O hydrogen bonds were in a significant role in packing, creating hydrogen-bonded dimers in 1B and 2B, and hydrogen-bonded chains in 5B.fi
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.ispartofseriesCrystal Growth and Design
dc.relation.urihttp://pubs.acs.org/doi/abs/10.1021/cg4005714
dc.rightsIn Copyright
dc.subject.otherkristallografia
dc.subject.otherorganic complexes
dc.titleCrystal Structures and Density Functional Theory Calculations of o-and p-Nitroaniline Derivatives: Combined Effect of Hydrogen Bonding and aromatic interactions on dimerization energy
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201401141053
dc.contributor.laitosFysiikan laitosfi
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Physicsen
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineFysiikkafi
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineNanoscience Centerfi
dc.contributor.oppiainePhysicsen
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineNanoscience Centeren
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2014-01-14T04:30:26Z
dc.description.reviewstatuspeerReviewed
dc.format.pagerange3603-3612
dc.relation.issn1528-7483
dc.relation.numberinseries8
dc.relation.volume13
dc.type.versionacceptedVersion
dc.rights.copyright© American Chemical Society, 2013
dc.rights.accesslevelopenAccessfi
dc.subject.ysoorgaaninen kemia
dc.subject.ysolaskennallinen kemia
dc.subject.ysokidetiede
jyx.subject.urihttp://www.yso.fi/onto/yso/p11902
jyx.subject.urihttp://www.yso.fi/onto/yso/p23053
jyx.subject.urihttp://www.yso.fi/onto/yso/p643
dc.rights.urlhttp://rightsstatements.org/page/InC/1.0/?language=en
dc.relation.doi10.1021/cg4005714


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