{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["15"],"submitter":["Francisco CB"],"pubmed_abstract":["The presence of strong stereoelectronic interactions involving the substituents in <i>cis</i>-2-substituted cyclohexanes may lead to results different from those expected. In this work, we studied the conformational behavior of <i>cis</i>-2-fluoro- (<b>F</b>), <i>cis</i>-2-chloro- (<b>Cl</b>), <i>cis</i>-2-bromo- (<b>Br</b>) and <i>cis</i>-2-iodocyclohexylamine (<b>I</b>) by dynamic NMR and theoretical calculations. The experimental data pointed to an equilibrium strongly shifted toward the <b>ea</b> conformer (equatorial amine group and axial halogen), with populations greater than 90% for <b>F</b>, <b>Cl</b> and <b>Br</b> in both dichloromethane-<i>d</i> <sub>2</sub> and methanol-<i>d</i> <sub>4</sub>. Theoretical calculations (M06-2X/6-311++G(2df,2p)) were in agreement with the experime"],"journal":["Beilstein journal of organic chemistry"],"pagination":["818-829"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC6466766"],"repository":["biostudies-literature"],"pubmed_title":["Strong hyperconjugative interactions limit solvent and substituent influence on conformational equilibrium: the case of <i>cis</i>-2-halocyclohexylamines."],"pmcid":["PMC6466766"],"pubmed_authors":["Basso EA","Francisco CB","Gauze GF","Fernandes CS","de Melo UZ","Rittner R"],"additional_accession":[]},"is_claimable":false,"name":"Strong hyperconjugative interactions limit solvent and substituent influence on conformational equilibrium: the case of <i>cis</i>-2-halocyclohexylamines.","description":"The presence of strong stereoelectronic interactions involving the substituents in <i>cis</i>-2-substituted cyclohexanes may lead to results different from those expected. In this work, we studied the conformational behavior of <i>cis</i>-2-fluoro- (<b>F</b>), <i>cis</i>-2-chloro- (<b>Cl</b>), <i>cis</i>-2-bromo- (<b>Br</b>) and <i>cis</i>-2-iodocyclohexylamine (<b>I</b>) by dynamic NMR and theoretical calculations. The experimental data pointed to an equilibrium strongly shifted toward the <b>ea</b> conformer (equatorial amine group and axial halogen), with populations greater than 90% for <b>F</b>, <b>Cl</b> and <b>Br</b> in both dichloromethane-<i>d</i> <sub>2</sub> and methanol-<i>d</i> <sub>4</sub>. Theoretical calculations (M06-2X/6-311++G(2df,2p)) were in agreement with the experime","dates":{"release":"2019-01-01T00:00:00Z","publication":"2019","modification":"2025-04-19T11:09:37.412Z","creation":"2019-06-06T22:56:20Z"},"accession":"S-EPMC6466766","cross_references":{"pubmed":["31019574"],"doi":["10.3762/bjoc.15.79"]}}