Abstract
Calculations of the charge of the pyrrolic nitrogen atom in the trail pheromone ofAtta texana, methyl 4-methylpyrrole-2-carboxylate, as well as 17 analogs, showed that the most active compounds all had the same charge of −0.51 electrons on the nitrogen atom. It is suggested that the close value for this charge may be important in recognition by the receptor.
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Clementi, E., andRaimondi, D.L. 1963. Atomic screening constants from SCF functions.J. Chem. Phys. 38:2686–2689.
Hoffmann, R. 1963. An extended Hückel theory. I. Hydrocarbons.J. Chem. Phys. 39:1397–1412.
Hoffmann, R. 1964a. Extended Hückel theory. III. Compounds of boron and nitrogen.J. Chem. Phys. 40:2474–2480.
Hoffmann, R. 1964b. Extended Hückel theory. IV. Carbonium ions.J. Chem. Phys. 40:2480–2488.
Hoffmann, R. 1964c. Extended Hückel theory. II. Orbitals in the azines.J. Chem. Phys. 40:2745.
Mulliken, R.S. 1955. Electronic population analysis on LCAO-MO molecular wave functions. I.J. Chem. Phys. 23:1833–1840.
Mulliken, R.S. 1955. Electronic population analysis on LCAO-MO molecular wave functions. II. Overlap populations, bond orders, and covalent bond energies.J. Chem. Phys. 23:1841–1846.
Payne, T.L. 1974. Pheromone perception, pp. 35–61, M.C. Birch (ed.).Pheromones. North-Holland Publishing, Amsterdam.
Sonnet, P.E., andMoser, J.C. 1972. Synthetic analogs of the trail pheromone of the leaf-cutting ant,Atta texana (Buckley).J. Agric. Food Chem. 20:1191–1194.
Sonnet, P.E., andMoser, J.C. 1973. Trail pheromones: Responses of the Texas leafcutting ant,Ana texana to selected halo- and cyanopyrrole-2-aldehydes, ketones, and esters.Environ. Entomol. 2:851–854.
Tumlinson, J.H., Silverstein, R.M., Moser, J.C., Brownlee, R.G., andRuth, J.M. 1971. Identification of the trail pheromone of the leaf-cutting ant,Atta texana. Nature 234:348–349.
Wolfsberg, M., andHelmholz, L. 1952. The spectra and electronic structure of the tetrahedral ions MnO −4 , CrO =4 , and CIO =4 .J. Chem. Phys. 20:837–843.
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This work was supported in part by the University of Iowa Computer Center.
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Caputo, J.F., Caputo, R.E. & Brand, J.M. Significance of the pyrrolic nitrogen atom in receptor recognition ofAtta texana (Buckley) (Hymenoptera:Formicidae) trail pheromone and parapheromones. J Chem Ecol 5, 273–278 (1979). https://doi.org/10.1007/BF00988241
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DOI: https://doi.org/10.1007/BF00988241