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dc.contributor.authorAl-Majid, Abdullah Mohammed
dc.contributor.authorHaukka, Matti
dc.contributor.authorSoliman, Saied M.
dc.contributor.authorAlamary, Abdullah Saleh
dc.contributor.authorAlshahrani, Saeed
dc.contributor.authorAli, M.
dc.contributor.authorIslam, Mohammad Shahidul
dc.contributor.authorBarakat, Assem
dc.date.accessioned2021-01-25T13:54:36Z
dc.date.available2021-01-25T13:54:36Z
dc.date.issued2021
dc.identifier.citationAl-Majid, A. M., Haukka, M., Soliman, S. M., Alamary, A. S., Alshahrani, S., Ali, M., Islam, M. S., & Barakat, A. (2021). X-ray Crystal Structure and Hirshfeld Analysis of Gem-Aminals-Based Morpholine, Pyrrolidine, and Piperidine Moieties. <i>Symmetry</i>, <i>13</i>(1), Article 20. <a href="https://doi.org/10.3390/sym13010020" target="_blank">https://doi.org/10.3390/sym13010020</a>
dc.identifier.otherCONVID_47832126
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/73787
dc.description.abstractThe gem-aminals of 1,2-dimorpholinoethane (1) and 1-morpholino-3-morpholinium bromide propane (2) were synthesized by reaction of two molar ratio of morpholine with the halogenating agents in the presence of basic condition (K2CO3) in acetone at room temperature (RT) overnight. The structures of the centro-symmetric compound 1 and the morpholinium salt derivative 2 were assigned unambiguous by single crystal X-ray diffraction analysis and compared with the 1,2-di(pyrrolidin-1-yl)ethane 3 and 1,2-di(piperidin-1-yl)ethane 4. The 1,2-dimorpholinoethane molecule has a center of symmetry at the midpoint of the C-C bond of the ethyl moiety leading to two equivalent halves. It crystallized in monoclinic crystal system and P21/n space group, while the unit cell parameters are determined to be a = 6.0430(3), b = 8.0805(3), c = 11.1700(4) Å, and β = 97.475(2)° with unit cell volume of 540.80(4) Å3 and Z = 2 at 170(2) K. The less symmetric analogue 2 crystallized in the lower space group P21 with unit cell parameters of a = 6.37450(10), b = 11.1378(2), c = 9.6549(2) Å, and β = 93.358(2)°, while the unit cell volume is 684.30(2)Å3 at 120(2) K. Using Hirshfeld analysis, the molecules of 1 are mainly packed by weak N…H (4.2%), O…H (16.8%), and H…H (79.0%) interactions. In contrast, the molecules of 2 are packed by significantly short O…H (14.4%) and Br…H (11.6%) interactions in addition to the relatively long H…H (73.3%) interactions. DFT calculations predicted the molecular geometry of the studied compounds showing a good agreement with the experimental X-ray structures. Due to symmetry considerations, compounds 1, 3, and 4 are nonpolar with zero dipole moment, while the less symmetric molecule 2 has a dipole moment of 6.914 Debye. Their electronic aspects, such as natural population charges, HOMO, and LUMO energies as well as the corresponding reactivity descriptors, were also calculated and discussed.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherMDPI AG
dc.relation.ispartofseriesSymmetry
dc.rightsCC BY 4.0
dc.subject.otheraminals
dc.subject.otherDFT
dc.subject.otherHirshfeld analysis
dc.subject.othermorpholine
dc.subject.otherpiperidine
dc.subject.otherpyrrolidine
dc.subject.otherX-ray
dc.titleX-ray Crystal Structure and Hirshfeld Analysis of Gem-Aminals-Based Morpholine, Pyrrolidine, and Piperidine Moieties
dc.typeresearch article
dc.identifier.urnURN:NBN:fi:jyu-202101251249
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen kemiafi
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineInorganic Chemistryen
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.relation.issn2073-8994
dc.relation.numberinseries1
dc.relation.volume13
dc.type.versionpublishedVersion
dc.rights.copyright© 2020 the Authors
dc.rights.accesslevelopenAccessfi
dc.type.publicationarticle
dc.subject.ysoamiinit
dc.subject.ysoorgaaniset yhdisteet
dc.subject.ysotiheysfunktionaaliteoria
dc.subject.ysoröntgenkristallografia
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p9219
jyx.subject.urihttp://www.yso.fi/onto/yso/p3841
jyx.subject.urihttp://www.yso.fi/onto/yso/p28852
jyx.subject.urihttp://www.yso.fi/onto/yso/p29058
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.3390/sym13010020
dc.type.okmA1


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