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dc.creatorBaranac-Stojanović, Marija
dc.creatorStojanović, Milovan
dc.creatorAleksić, Jovana
dc.date.accessioned2019-06-29T11:16:47Z
dc.date.available2018-05-03
dc.date.issued2017
dc.identifier.issn1144-0546
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/2969
dc.description.abstractThe strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.en
dc.publisherRoyal Soc Chemistry, Cambridge
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172020/RS//
dc.rightsembargoedAccess
dc.sourceNew Journal of Chemistry
dc.titleTheoretical study of azido gauche effect and its originen
dc.typearticle
dc.rights.licenseBY-NC-ND
dcterms.abstractБаранац-Стојановиц, Марија; Aлексић, Јована; Стојановић, Милован;
dc.citation.volume41
dc.citation.issue11
dc.citation.spage4644
dc.citation.epage4661
dc.citation.other41(11): 4644-4661
dc.citation.rankM22
dc.description.otherThis is the peer-reviewed version of the article: M. Baranac-Stojanovic, M. Stojanovic and J. Aleksic, New Journal of Chemistry, 2017, 41, 11, 4644-4661, [https://dx.doi.org/10.1039/C7NJ00369B]
dc.description.other[http://cer.ihtm.bg.ac.rs/handle/123456789/2264]
dc.identifier.doi10.1039/c7nj00369b
dc.identifier.rcubConv_3731
dc.identifier.fulltexthttp://cer.ihtm.bg.ac.rs/bitstream/id/7275/3_2906_C7NJ00369B.pdf
dc.identifier.scopus2-s2.0-85021676909
dc.identifier.wos000402377400045
dc.type.versionacceptedVersion


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