Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group
We report a conformational and electronic study of the sex pheromone of the pine processionary moth, Thaumetopoea pytiocampa, the (Z)-13-hexadecen-11-ynyl acetate (1) as well as the electronic properties of a few analogues, which were obtained by substitutions on the methyl group at the acetate f...
Guardado en:
| Autores principales: | , , , |
|---|---|
| Formato: | Artículo |
| Lenguaje: | Inglés |
| Publicado: |
Asociación Química Argentina
2024
|
| Materias: | |
| Acceso en línea: | http://repositorio.unne.edu.ar/handle/123456789/53091 |
| Aporte de: |
| id |
I48-R184-123456789-53091 |
|---|---|
| record_format |
dspace |
| spelling |
I48-R184-123456789-530912025-03-06T11:05:41Z Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group Chamorro, Ester Ramona Benítez, Elisa Inés Sequeira, Alfredo Fabián Peruchena, Nélida María Conformational analysis Charge density Am1 Theoretical calculations Molecular orbital theory Sex pheromone Semiempirical methods Análisis conformacional Densidad de carga Cálculos teóricos Teoría de orbitales moleculares Feromonas sexuales Métodos semiempíricos We report a conformational and electronic study of the sex pheromone of the pine processionary moth, Thaumetopoea pytiocampa, the (Z)-13-hexadecen-11-ynyl acetate (1) as well as the electronic properties of a few analogues, which were obtained by substitutions on the methyl group at the acetate function of the molecule (–OCO–R with R= –CH3 (1); –CH2F (2); –CF3 (3); –CH2CH3 (4); –H (5); –CH2Cl (6) and –CCl3 (7)). Analogue derivative (8) is also included, where –OCO is substituted by –SCO. An exploratory study of the conformational energy surface at compound 1 was carried out varying the torsion angles around C1–O, (φ1); O–C(=O), (φ2) and C9–C10, (φ3) bonds, using semiempirical methods. The structural and electronic parameters as atomic charges and orbital energies were calculated. Total Electronic Charge Density maps were also determined for the pheromone molecule and their analogue derivatives. The results obtained at semiempirical level of theory with AM1 Hamiltonian were related to the stereoelectronic requirements necessary to produce the activity on biological receptor, by comparative electroantennogram responses, EAG. Nosotros presentamos un estudio conformacional y electrónico de la feromona sexual de la mariposa de la procesionaria del pino, Thaumetopoea pytiocampa, el acetato de (Z)-13- hexadecen-11-inilo (1) así como las propiedades electrónicas de unos pocos análogos obtenidos por sustitución sobre el grupo metilo en la función acetato de la molécula (–OCO– R con R= –CH3 (1); –CH2F (2); –CF3 (3); –CH2CH3 (4); –H (5); –CH2Cl (6) y –CCl3 (7)). También se incluye el análogo (8) donde –OCO se reemplazó por –SCO. Se realizó un estudio exploratorio de la superficie de energía conformacional en el compuesto 1, empleando métodos semiempíricos, variando los ángulos de torsión alrededor de los enlaces C1–O, (φ1); O–C(=O), (φ2) y C9–C10, (φ3). Se calcularon parámetros estructurales y electrónicos como cargas atómicas y energías orbitales. También fueron determinados los mapas de densidad de carga electrónica total para la molécula de feromona y sus análogos. Los resultados obtenidos, a nivel semiempírico con Hamiltoniano AM1, fueron analizados en forma conjunta con los resultados obtenidos por electroantenografía, EAG, y relacionados con los requerimientos estereoelectrónicos necesarios para producir la actividad biológica. 2024-03-06T10:50:15Z 2024-03-06T10:50:15Z 2008 Artículo Chamorro, Ester Ramona, et al., 2008. Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group. Journal of the Argentine Chemical Society. Buenos Aires: Asociación Química Argentina, vol. 96, no.1-2, p. 62-79. E-ISSN 1852-1207. http://repositorio.unne.edu.ar/handle/123456789/53091 eng https://www.aqa.org.ar/images/anales/pdf9612/9612art7.pdf openAccess http://creativecommons.org/licenses/by-nc-nd/2.5/ar/ application/pdf p. 62-79 application/pdf Asociación Química Argentina Journal of the Argentine Chemical Society, 2008, vol. 96, no. 1-2, p. 62-79. |
| institution |
Universidad Nacional del Nordeste |
| institution_str |
I-48 |
| repository_str |
R-184 |
| collection |
RIUNNE - Repositorio Institucional de la Universidad Nacional del Nordeste (UNNE) |
| language |
Inglés |
| topic |
Conformational analysis Charge density Am1 Theoretical calculations Molecular orbital theory Sex pheromone Semiempirical methods Análisis conformacional Densidad de carga Cálculos teóricos Teoría de orbitales moleculares Feromonas sexuales Métodos semiempíricos |
| spellingShingle |
Conformational analysis Charge density Am1 Theoretical calculations Molecular orbital theory Sex pheromone Semiempirical methods Análisis conformacional Densidad de carga Cálculos teóricos Teoría de orbitales moleculares Feromonas sexuales Métodos semiempíricos Chamorro, Ester Ramona Benítez, Elisa Inés Sequeira, Alfredo Fabián Peruchena, Nélida María Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group |
| topic_facet |
Conformational analysis Charge density Am1 Theoretical calculations Molecular orbital theory Sex pheromone Semiempirical methods Análisis conformacional Densidad de carga Cálculos teóricos Teoría de orbitales moleculares Feromonas sexuales Métodos semiempíricos |
| description |
We report a conformational and electronic study of the sex pheromone of the pine
processionary moth, Thaumetopoea pytiocampa, the (Z)-13-hexadecen-11-ynyl acetate (1) as
well as the electronic properties of a few analogues, which were obtained by substitutions on
the methyl group at the acetate function of the molecule (–OCO–R with R= –CH3 (1); –CH2F
(2); –CF3 (3); –CH2CH3 (4); –H (5); –CH2Cl (6) and –CCl3 (7)). Analogue derivative (8) is
also included, where –OCO is substituted by –SCO. An exploratory study of the conformational energy surface at compound 1 was carried
out varying the torsion angles around C1–O, (φ1); O–C(=O), (φ2) and C9–C10, (φ3) bonds,
using semiempirical methods. The structural and electronic parameters as atomic charges and
orbital energies were calculated. Total Electronic Charge Density maps were also determined
for the pheromone molecule and their analogue derivatives. The results obtained at
semiempirical level of theory with AM1 Hamiltonian were related to the stereoelectronic
requirements necessary to produce the activity on biological receptor, by comparative
electroantennogram responses, EAG. |
| format |
Artículo |
| author |
Chamorro, Ester Ramona Benítez, Elisa Inés Sequeira, Alfredo Fabián Peruchena, Nélida María |
| author_facet |
Chamorro, Ester Ramona Benítez, Elisa Inés Sequeira, Alfredo Fabián Peruchena, Nélida María |
| author_sort |
Chamorro, Ester Ramona |
| title |
Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group |
| title_short |
Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group |
| title_full |
Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group |
| title_fullStr |
Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group |
| title_full_unstemmed |
Conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group |
| title_sort |
conformational and electronic study of sex pheromone of the pine processionary moth and some related derivative compounds with modification in the polar group |
| publisher |
Asociación Química Argentina |
| publishDate |
2024 |
| url |
http://repositorio.unne.edu.ar/handle/123456789/53091 |
| work_keys_str_mv |
AT chamorroesterramona conformationalandelectronicstudyofsexpheromoneofthepineprocessionarymothandsomerelatedderivativecompoundswithmodificationinthepolargroup AT benitezelisaines conformationalandelectronicstudyofsexpheromoneofthepineprocessionarymothandsomerelatedderivativecompoundswithmodificationinthepolargroup AT sequeiraalfredofabian conformationalandelectronicstudyofsexpheromoneofthepineprocessionarymothandsomerelatedderivativecompoundswithmodificationinthepolargroup AT peruchenanelidamaria conformationalandelectronicstudyofsexpheromoneofthepineprocessionarymothandsomerelatedderivativecompoundswithmodificationinthepolargroup |
| _version_ |
1832345427506102272 |