Determination of the preferred conformation of the bicyclic Galerucella pheromone using density functional theory optimization and calculations of chemical shifts

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 4748-4758

  Bosma, Wayne B ^a   Bartelt, Robert J ^b   Momany, Frank A ^b  

^a BRADLEY UNIVERSITY   (United States)

^b NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL SHIFTS; GAUGE-INCLUDING ATOMIC ORBITAL (GIAO); LOW-ENERGY MINIMA; TRANSITION STATES;

COMPOSITION; CONFORMATIONS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTIMIZATION; ORGANIC COMPOUNDS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

HORMONES;

12,13 DIMETHYL 5,14 DIOXABICYCLO[9.2.1]TETRADECA 1(13),11 DIEN 4 ONE; BICYCLO COMPOUND; FURAN DERIVATIVE; LACTONE DERIVATIVE; PHEROMONE; TETRADECANE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ANALYTIC METHOD; ARTICLE; BEETLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; DENSITY FUNCTIONAL THEORY; DIHEDRAL DRIVING TECHNIQUE; ENERGY; GALERUCELLA CALMARIENSIS; GAUGE INCLUDING ATOMIC ORBITAL METHOD; MODE FOLLOWING TECHNIQUE; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; TECHNIQUE;

ANIMALS; BEETLES; BICYCLO COMPOUNDS, HETEROCYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHEROMONES; REFERENCE STANDARDS; SENSITIVITY AND SPECIFICITY;

EID: 33745469199     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0524730     Document Type: Article

References (17)

1. Bartelt, R. J.; Cosse, A. A.; Zilkowski, B. W.; Weisleder, D.; Grode, S. H.; Wiedenmann, R. N. L.; Post, S. L. J. Chem. Ecol. 2006, 32, 693-712.
2. Ditchfield, R. Mol. Phys. 1974, 27, 789-807.
3. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
4. Wiberg, K. B. J. Comput. Chem. 2004, 25, 1342-1346.
5. Wiberg, K. B. J. Comput. Chem. 1999, 20, 1299-1303.
6. Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497-5509.
7. Rauhut, G.; Puyear, S.; Wolinski, K.; Pulay, P. J. Phys. Chem. 1996, 100, 6310-6316.
8. Karplus, M. J. Chem. Phys. 1959, 30, 11-15.
9. Ab Initio Program Package, version 3.1; Parallel Quantum Solutions: 2013 Green Acres, Suite A, Fayetteville, AR 72703.
10. InsightII/Discover, Accelrys Software Inc.: 10188 Telesis Court, Suite 100, San Diego, CA 92121.
11. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Could, I. R.; Merz, K., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5197.
12. Baker, J.; Kinghorn, D.; Pulay, P. J. Chem. Phys. 1999, 110, 4986-4991.
13. Fukui, K. J. Phys. Chem. 1970, 74, 4161-4163.
14. Schmidt, M. W.; Gordon, M. S.; Dupuis, M. J. Am. Chem. Soc. 1985, 107, 2585-2589.
15. Anet, F. A. L.; Cheng, A. K.; Krane, J. J. Am. Chem. Soc. 1973, 95, 7877-7878.
16. Burkert, U.; Allinger, N. L. J. Comput. Chem. 1982, 3, 40-46.
17. Laszlo, P. Prog. Nucl. Magn. Reson. Spectrosc. 1967, 3, 231-402.