Replacement of the terminal methyl group in a moth sex pheromone component by a 
halogen atom: Hydrophobicity and size effects on electrophysiological 
single-cell activities

Jönsson, S.; Liljefors, T.; Hansson, B. S.

doi:10.1007/bf00983771

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Replacement of the terminal methyl group in a moth sex pheromone component by a halogen atom: Hydrophobicity and size effects on electrophysiological single-cell activities

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Jönsson, S., Liljefors, T., & Hansson, B. S. (1991). Replacement of the terminal methyl group in a moth sex pheromone component by a halogen atom: Hydrophobicity and size effects on electrophysiological single-cell activities. Journal of Chemical Ecology, 17(7), 1381-1397. doi:10.1007/bf00983771.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-5E45-6

Abstract

Analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, with a chloro, bromo, or iodo substituent in place of the terminal methyl group have been synthesized and tested by electrophysiological single-sensillum recordings. The electrophysiological results have been interpreted in terms of substituent size and hydrophobicity. Interaction energies based on receptor interaction models have been calculated using the molecular mechanics [MM2(85)] method. The results support our previously suggested receptor interaction model in which the terminal alkyl chain interact with a complementary hydrophobic receptor "pocket" with very limited flexibility.