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Volumn 112, Issue 50, 2008, Pages 12849-12854

The different aromatic characters of some localized benzene derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AROMATICITY; BENZENE DERIVATIVES; MODEL COMPOUNDS; RING CURRENTS;

EID: 58149164887     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp801634x     Document Type: Article
Times cited : (23)

References (34)
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    • (b) It was later shown also bv the MO method within the HF/3-21G theoretical level. Stanger, A.; Vollhardt, K. P. C. J. Org. Chem. 1988, 53, 4889-4890.
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    • For a recent summary of the topic, see:, John Wiley & Sons, Inc, Hoboken, New Jersey, and references therein
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    • Frisch, M. J. Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda. Y.; Kitao, O.; Nakai. H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
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    • ASE cannot be regarded as a general method to assess aromaticity. For example, when applied to inorganic benzene analogues (e.g., borazine), the protonation of the open-chain analogue is a lone pair protonation, which is very different from protonation of hexatriene. The aromaticity assessments obtained by this method are thus questionable. See, for example: Kiran, B.; Kumar, A.; Jemmis, E. D. Inorg. Chem 2001, 40, 3615.
    • (a) ASE cannot be regarded as a general method to assess aromaticity. For example, when applied to "inorganic benzene" analogues (e.g., borazine), the protonation of the open-chain analogue is a lone pair protonation, which is very different from protonation of hexatriene. The aromaticity assessments obtained by this method are thus questionable. See, for example: Kiran, B.; Kumar, A.; Jemmis, E. D. Inorg. Chem 2001, 40, 3615.
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    • The hydrogenation product of 1 is planar. See: Mohler, D. L.; Vollhardt, K. P. C.; Wolff, S. Angew. Chem., Int. Ed. Engl. 1990, 29, 1151-1154.
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    • Experimental data taken from NIST Chemistry WebBook, see
    • Experimental data taken from NIST Chemistry WebBook, see http://webbook.nist.gov/chemistry/.
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    • (b) Stanger, A. Chem- Eur. J. 2006, 12, 2745-2751.[27] It is noted that the four- and six-membered rings are conjugated. Thus, the NICS values of each ring are influenced by the annulated ring(s).
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    • 6h planar-annulene, which includes three imaginary frequencies, was used.
    • 6h planar-annulene, which includes three imaginary frequencies, was used.
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    • For the definition of SIBL, see ref 16
    • For the definition of SIBL, see ref 16.
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    • is not a minimum on the potential surface and contains eight imaginary frequencies
    • 3h 14 is not a minimum on the potential surface and contains eight imaginary frequencies.
    • 3h , vol.14
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    • Note that the central six-membered ring in optimized 14 is nonplanar. Thus, the distance for the minimum value of the out-of-plane component of the NICS is from an averaged point, not from the ring plane as that in the D3h species
    • 3h species.
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    • It was already noted that removal of the symmetry from the Hückel matrix will result in lower energv. See: Heilbronner, E. J. Chem. Educ. 1989, 66, 471-478
    • It was already noted that removal of the symmetry from the Hückel matrix will result in lower energv. See: Heilbronner, E. J. Chem. Educ. 1989, 66, 471-478.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.