Theoretical Analysis of Reactivity and Regioselectivity in [1+2] Cycloaddtion Reaction of some Monoterpenes with Dichlorocarbene

A. Zeroual

Authors

A. Zeroual

[1 2] cycloaddition, limonene, terpinolene, ?- terpinene, DFT/6-31(d, p), TST

Abstract

A theoretical study of the molecular mechanism and regioselectivity of the [1+2] cycloaddition reaction between alkenes: limonene, terpinolene, γ-terpinene and dichlorocarbene has been carried out at the B3LYP/6-31G (d,p) level of theory. The calculation of activation and reaction free energies indicates that these reactions are regio-specific in good agreement with experimental result.

Downloads

How to Cite

Theoretical Analysis of Reactivity and Regioselectivity in [1+2] Cycloaddtion Reaction of some Monoterpenes with Dichlorocarbene. (2017). Global Journal of Science Frontier Research, 17(B1), 7-14. https://journalofscience.org/index.php/GJSFR/article/view/1972

Download Citation

References

D Panayotopoulos, D Chisholm (1970) Hallucinogenic effect of nutmeg.. 1(5698), 754.1-754.

Abdul Wahab, Rizwan Haq, Aftab Ahmed, Rafeeq Khan, Mohsin Raza (2009) Anticonvulsant activities of nutmeg oil of Myristica fragrans. 23(2), 153-158.

G Sonavane, V Sarveiya, V Kasture, S Kasture (2001) Anxiogenic activity of Myristica fragrans seeds. 71(1-2), 239-244.

S Darbar, A Bhattacharya, S Chattopadhyay (2011) antihepatoprotective potential of livina, a polyherbal preparation on paracetamol induced hepatotoxicity: a comparison with silymarin. 4, 72-77.

K Hammer, C Carson, T Riley (2003) Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil. 95(4), 853-860.

Younis Hamad (2014) Role of Essential Oils in Controlling Fungi that Cause Decline Disease of Guava. 3(5), 143-151.

S Combrinck, T Regnier, G Kamatou (2011) In vitro activity of eighteen essential oils and some major components against common postharvest fungal pathogens of fruit. 33, 344-349.

Akiko Takikawa, Keiko Abe, Makiko Yamamoto, Shoko Ishimaru, Mari Yasui, Yoko Okubo, Kumio Yokoigawa (2002) Antimicrobial Activity of Nutmeg against Escherichia coli O157. 94(4), 315-320.

P Delaquis, K Stanich, B Girard, G Mazza (2002) Antimicrobial activity of individual and mixed fractions of dill, cilantro, coriander and eucalyptus essential oils. 74(1-2), 101-109.

B Damjanovic´-Vratnica, T Đakov, D Šukovic, J Damjanovic´ (2011) Antimicrobial effect of essential oil isolated from Eucalyptus globulus Labill. from Montenegro. 29, 277-284.

C Busatta, R Vidal, A Popiolski, A Mossi, C Dariva, M Rodrigues, F Corazza, M Corazza, J Vladimir, R Oliveira, Cansian (2008) Application of Origanum majorana L. essential oil as an antimicrobial agent in sausage. 25, 207-211.

Patrícia Sartorelli, Alexandre Marquioreto, Adriana Amaral‐baroli, Marcos Lima, Paulo Moreno (2007) Chemical composition and antimicrobial activity of the essential oils from two species of Eucalyptus. 21(3), 231-233.

O Olajide, F Ajiya, A Ekhelar, S Awe, J Makinde, A (1999) Alada Biological effects of Myristica fragrans (nutmeg) extract. 13, 344-345.

I Rasooli, S Mirmostafa (2002) Antibacterial properties of Thymus pubescens and Thymus serpyllum essential oils. 73, 244-250.

H Dorman, S Deans (2000) Antimicrobial agents from plants: antibacterial activity of plant volatile oils. 88(2), 308-316.

Seyed Nabavi, Anna Marchese, Morteza Izadi, Valeria Curti, Maria Daglia, Seyed Nabavi (2015) Plants belonging to the genus Thymus as antibacterial agents: From farm to pharmacy. 173, 339-347.

N Lan-Phi, T Vy (2015) Unknown Title. 22, 2426-2431.

J Koudou, L Obame, B Kumulungui, P Edou, G Figueredo, J Chalchat, A Traore (2009) Unknown Title. 3, 323-326.

S Guzmán-Gutiérrez, R Gómez-Cansino, J García-Zebadúa, N Jiménez-Pérez, R Reyes-Chilpa (2012) Antidepressant activity of Litsea glaucescens essential oil: Identification of β-pinene and linalool as active principles. 143(2), 673-679.

Tatsuya Morita, Keiko Jinno, Hirokazu Kawagishi, Yasushi Arimoto, Hiroyuki Suganuma, Takahiro Inakuma, Kimio Sugiyama (2003) Hepatoprotective Effect of Myristicin from Nutmeg (Myristica fragrans) on Lipopolysaccharide/d-Galactosamine-Induced Liver Injury. 51(6), 1560-1565.

Hossni Ziyat, My Itto, Mustapha Ali, Abdelkhalek Riahi, Abdellah Karim, Jean-Claude Daran (2006) Convenient synthesis of new functionalized cyclopropanes from monoterpenic olefines. 2006(12), 152-160.

K Fukui (1970) Formulation of the reaction coordinate. 74, 4161-4163.

Robert Parr, László Szentpály, Shubin Liu (1999) Electrophilicity Index. 121(9), 1922-1924.

Robert Parr, Ralph Pearson (1983) Absolute hardness: companion parameter to absolute electronegativity. 105(26), 7512-7516.

Luis Domingo, Patricia Pérez (2011) The nucleophilicity N index in organic chemistry. 9(20), 7168.

G Kresse, J Furthmüllerb (1996) Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set. 6, 15-50.

Abdellah Zeroual, Ahmed Benharref, Abdeslam El Hajbi (2015) 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). 21(3), 2594-2599.

Luis Domingo, Mar Ríos-Gutiérrez, Saeedreza Emamian (2016) Understanding the stereoselectivity in Brønsted acid catalysed Povarov reactions generating cis/trans CF₃-substituted tetrahydroquinolines: a DFT study. 6(21), 17064-17073.

D Jornet, F Bosca, J Andreu, L Domingo, R Tormos, M Miranda (2016) Analysis of mebendazole binding to its target biomolecule by laser flash photolysis. 155, 1-6.

A Zeroual, R Hammal, A Hajbi (2015) A DFT Study of the [1+2] cycloaddition reactions of 2-[1, 3]dioxolan-2-ylidene-malononitrile, TCE and chlorocarbene. 5, 97-101.

Abdellah Zeroual, Ahmed Benharref, Abdeslam El Hajbi (2015) 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). 21(3), 698-704.

Luis Domingo, Mar Ríos-Gutiérrez, Patricia Pérez (2016) A new model for C-C bond formation processes derived from the Molecular Electron Density Theory in the study of the mechanism of [3+2] cycloaddition reactions of carbenoid nitrile ylides with electron-deficient ethylenes. 72, 1524-1532.

A Zeroual, M Zoubir, R Hammal, A Benharref, A Hajbi (2015) Understanding the Regioselectivity and Reactivity of Friedel-Crafts benzoylation Using Parr Functions. 3, 356-360.

A Zeroual, R Hammal, K Ryachi, A Barhoumi, A Benharref, A Hajbi (2014) Understanding the Regioselectivity and Reactivity of [Beta]-Himachalene Using Zeroual Function as a new Regioselectivity Descriptor. 8, 750-755.

A Zeroual, A (2015) Understanding the Regioselective and Molecular Mechanism of the TCE in Cycloaddtion Reaction (TCE+Cp) and Addition Reaction (TCE+HCl) using DFT calculation. 3, 430-437.