Benzocyclynes adhere to Huckel's rule by the ring current criterion in experiment (1H NMR) and theory (NICS)

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6791-6794

  Matzger, Adam J ^a   Vollhardt, K Peter C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Annulenes; Aromaticity; Cycloalkynes; NMR

Indexed keywords

ANNULENE DERIVATIVE; BENZOCYCLYNE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; EXPERIMENT; PROTON NUCLEAR MAGNETIC RESONANCE; THEORY;

EID: 0032541731     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01441-5     Document Type: Article

References (34)

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20. β.
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25. (b) The δ values reported for benzo[c]cycloocta-1,5-diyne (Hopf, H.; Jones, P.G.; Bubenitschek, P.; Werner, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2367) are identical to those of 1,2-(1-pentynyl)benzene (Evenzahav, A.; Turro, N.J. J. Am. Chem. Soc. 1998, 120, 1835.
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28. (b) Calculations were executed at he B3LYP/6-31G* level, with fully optimized structures (ghost atoms at the ring centroids), using the GAUSSIAN-94 program, Revision B.1: Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Gill, P.M.W.; Johnson, B.G.; Robb, M.A.; Cheeseman, J.R.; Keith, T.A.; Peterson, G.A.; Montgomery, J.A.; Raghavachari, K.; Al-Lahm, M.A.; Zakrzewski, V.G.; Ortiz, J.V.; Foresman, J.B.; Cioslowski, J.; Stefanov, B.R. Nanayakkara, A.; Challacombe, M.; Peng, C.Y., Ayala, P.Y.; Chen, W.; Wong, M.W.; Andres, J.L.; Replogle, E.S.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Binkely, J.S.; Defrees, D.J.; Baker, J.; Stewart, J.P.; Head-Gordon, M.; Gonzales, C.; Pople, J.A. Gaussian, Inc.; Pittsburgh, PA, 1995.
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