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)
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| 024 | 7 | 0 | |a 10.1007/s00894-015-2594-4 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2594-4 | ||
| 245 | 0 | 0 | |a 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) |h [Elektronische Daten] |c [Abdellah Zeroual, Ahmed Benharref, Abdeslam El Hajbi] |
| 520 | 3 | |a 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. | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a 1 + 2 cycloaddition |2 nationallicence | |
| 690 | 7 | |a β-himachalene |2 nationallicence | |
| 690 | 7 | |a B3LYP/6-31G*(d) |2 nationallicence | |
| 690 | 7 | |a Charge transfer |2 nationallicence | |
| 690 | 7 | |a Chemospecificity |2 nationallicence | |
| 690 | 7 | |a Density functional theory |2 nationallicence | |
| 690 | 7 | |a Exothermic reaction |2 nationallicence | |
| 690 | 7 | |a Regioselectivity |2 nationallicence | |
| 690 | 7 | |a Stereoselectivity |2 nationallicence | |
| 700 | 1 | |a Zeroual |D Abdellah |u Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco |4 aut | |
| 700 | 1 | |a Benharref |D Ahmed |u Biomolecular Chemistry Laboratory, Natural Substances and Reactivity, URAC 16, Semlalia Faculty of Science, Cadi Ayyad University, BP 2390, 40000, Marrakech, Morocco |4 aut | |
| 700 | 1 | |a El Hajbi |D Abdeslam |u Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/3(2015-03-01), 1-6 |x 1610-2940 |q 21:3<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2594-4 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2594-4 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Zeroual |D Abdellah |u Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Benharref |D Ahmed |u Biomolecular Chemistry Laboratory, Natural Substances and Reactivity, URAC 16, Semlalia Faculty of Science, Cadi Ayyad University, BP 2390, 40000, Marrakech, Morocco |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a El Hajbi |D Abdeslam |u Physical Chemistry Laboratory, Chemistry Department, Faculty of Science, Chouaïb Doukkali University, BP 20, 24000, El Jadida, Morocco |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/3(2015-03-01), 1-6 |x 1610-2940 |q 21:3<1 |1 2015 |2 21 |o 894 | ||