caa a22 4500 605511845 CHVBK 20210128100653.0 cr unu---uuuuu 210128e20150301xx s 000 0 eng 10.1007/s00894-015-2594-4 doi (NATIONALLICENCE)springer-10.1007/s00894-015-2594-4 Theoretical study of stereoselectivity of the [1 + 2] cycloaddition reaction between (1S,3R,8S)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6,4,0,01.3]dodec-9-ene and dibromocarbene using density functional theory (DFT) B3LYP/6-31G*(d) [Elektronische Daten] [Abdellah Zeroual, Ahmed Benharref, Abdeslam El Hajbi] In this work we used density functional theory (DFT) B3LYP/6-31G*(d) to study the stoichiometric reaction between the product (1S,3R,8S)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6,4,0,01.3]dodec-9-ene (referred to here as P1) and dibromocarbene. We have shown that P1 behaves as a nucleophile, while dibromocarbene behaves as an electrophile; that the chemical potential of dibromocarbene is superior to that of P1 in absolute terms; and that P1 reacts with an equivalent quantity of dibromocarbene to produce two products: (1S,3R,8R,9S,11R)-10,10-dibromo-2,2-dichloro-3,7,7,11-tetramethyltetracyclo[6,5,0,01.3,09.11] tridecane (referred to here as P2) and (1S,3R,8R,9R,11S)-10,10-dibromo-2,2-dichloro-3,7,7,11-tetramethyltetracyclo[6,5,0,01.3,09.11] tridecane (referred to here as P3). P2 and P3 are formed at the α and β sides, respectively, of the C2 = C3 double bond of P1. This reaction is exothermic, stereoselective and chemospecific, and is controlled by charge transfer. Regioselectivity of the reaction was interpreted using the Lee-Yang-Parr functional. Springer-Verlag Berlin Heidelberg, 2015 1 + 2 cycloaddition nationallicence β-himachalene nationallicence B3LYP/6-31G*(d) nationallicence Charge transfer nationallicence Chemospecificity nationallicence Density functional theory nationallicence Exothermic reaction nationallicence Regioselectivity nationallicence Stereoselectivity nationallicence Zeroual Abdellah Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco aut Benharref Ahmed Biomolecular Chemistry Laboratory, Natural Substances and Reactivity, URAC 16, Semlalia Faculty of Science, Cadi Ayyad University, BP 2390, 40000, Marrakech, Morocco aut El Hajbi Abdeslam Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/3(2015-03-01), 1-6 1610-2940 21:3<1 2015 21 894 https://doi.org/10.1007/s00894-015-2594-4 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2594-4 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Zeroual Abdellah Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco aut NATIONALLICENCE 700 1- Benharref Ahmed Biomolecular Chemistry Laboratory, Natural Substances and Reactivity, URAC 16, Semlalia Faculty of Science, Cadi Ayyad University, BP 2390, 40000, Marrakech, Morocco aut NATIONALLICENCE 700 1- El Hajbi Abdeslam Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/3(2015-03-01), 1-6 1610-2940 21:3<1 2015 21 894