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Contribution of hyperconjugation and inductive effects to the pseudo-anomeric effect in 4-substituted methoxycyclohexanes

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dc.contributor.authorPiscelli, Bruno A.
dc.contributor.authorO’Hagan, David
dc.contributor.authorCormanich, Rodrigo A.
dc.date.accessioned2024-01-17T00:35:12Z
dc.date.available2024-01-17T00:35:12Z
dc.date.issued2023-01-26
dc.identifier282994871
dc.identifiercbb67c75-b3ef-4a5b-abff-9cc525127a44
dc.identifier85146578588
dc.identifier000921923700001
dc.identifier.citationPiscelli , B A , O’Hagan , D & Cormanich , R A 2023 , ' Contribution of hyperconjugation and inductive effects to the pseudo -anomeric effect in 4-substituted methoxycyclohexanes ' , Journal of Physical Chemistry A , vol. 127 , no. 3 , pp. 724–728 . https://doi.org/10.1021/acs.jpca.2c08090en
dc.identifier.issn1089-5639
dc.identifier.otherRIS: urn:0B09FD4F073B17FBC0FF4B87F2F9C923
dc.identifier.otherORCID: /0000-0002-0510-5552/work/127065440
dc.identifier.urihttps://hdl.handle.net/10023/29022
dc.descriptionFunding: We gratefully acknowledge FAPESP for a PhD scholarship to B.A.P. (#2021/09716-5) and a Young Research Award to R.A.C. (#2018/03910-1) and FAEPEX for a fellowship (2479/21).en
dc.description.abstractThe importance of electrostatic nonconventional hydrogen bonds (NCHBs) to the pseudo-anomeric effect of 4-substituted methoxycyclohexanes is evaluated using theory [natural bond orbital (NBO)] to deconvolute electrostatic from other contributing effects. There is an interesting interplay between σCH → σCX* hyperconjugation and the electropositive charge on 3,5-axial hydrogens (Hax). In essence, better σCX* (or πCO*) acceptors increase the charge on 3,5-CHax, which in turn strengthens Cδ+Hax···δ−OMe NCHB interactions.
dc.format.extent5
dc.format.extent1284185
dc.format.extent7718596
dc.language.isoeng
dc.relation.ispartofJournal of Physical Chemistry Aen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subjectACen
dc.subjectMCCen
dc.subject.lccQDen
dc.titleContribution of hyperconjugation and inductive effects to the pseudo-anomeric effect in 4-substituted methoxycyclohexanesen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. Institute of Behavioural and Neural Sciencesen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doi10.1021/acs.jpca.2c08090
dc.description.statusPeer revieweden
dc.date.embargoedUntil2024-01-17


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