84. The crystal structure of an overcrowded aromatic compound: 3-bromo-1,8-dimethylnaphthalene

Jameson, M. B.; Penfold, B. R.

doi:10.1039/jr9650000528

Cited by 25 publications

(17 citation statements)

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“…Similar features were also found in the crystal structure of the related compound 3-bromo-1,8-dimethylnaphthalene. 14 In the present study this feature is more apparent at higher temperatures. We also Ðnd here that the lengthening is not symmetrical about carbon C9 ; the di †erence between bond lengths C8-C9 and C8-C7 is always greater than the di †erence between C1-C2 and C1-C9 by approximately 0.04 This A .…”

Section: Resultssupporting

confidence: 55%

Methyl group librations in sterically hindered dimethylnaphthalene molecules: neutron diffraction studies of 1,8-dimethylnaphthalene between 50 and 200 K

Wilson

Nowell

2000

New J. Chem.

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The structure of 1,8-dimethylnaphthalene has been studied by variable temperature single crystal neutron di †raction. The location of the two methyl groups on the same side of the naphthalene ring leads to substantial steric e †ects, notably a hindering of the methyl group librations. This steric e †ect appears to dominate over the alternative possibility of coupled motions of these groups. The results are compared directly with those from the related compound 1,5-dimethylnaphthalene where there is no possibility of methyl group coupled motions, but also less severe steric hindrance.

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Section: Resultssupporting

confidence: 55%

Methyl group librations in sterically hindered dimethylnaphthalene molecules: neutron diffraction studies of 1,8-dimethylnaphthalene between 50 and 200 K

Wilson

Nowell

2000

New J. Chem.

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“…(Chanh et al, 1976) The average C-C distance in 1 (1.397 Å) is within the range attributed for aromatic C-C bonds in bromine containing naphthalene products (Bienko et al, 2003;Brady et al, 1982;Chanh et al, 1973;Jameson & Penfold, 1965;and McCarthy & Huffman, 1984) and compares to the average C-C distance observed for 2 (1.403 Å). (Chanh et al, 1976) The average C-C distance in 1 (1.397 Å) is within the range attributed for aromatic C-C bonds in bromine containing naphthalene products (Bienko et al, 2003;Brady et al, 1982;Chanh et al, 1973;Jameson & Penfold, 1965;and McCarthy & Huffman, 1984) and compares to the average C-C distance observed for 2 (1.403 Å).…”

Section: Commentmentioning

confidence: 66%

“…For related literature, see: Bienko et al (2003); Brady et al (1982); Chanh et al (1973Chanh et al ( , 1976; Gao et al (2005); Jameson & Penfold (1965); McCarthy & Huffman (1984); Sigouin et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

6-Bromo-N-methylnaphthalen-2-amine

2007

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“…Distortion of the naphthalene ring is too small to be observed by E.P.R. although it is likely to have occurred to help alleviate the steric interaction of the/3ax protons in much the same way as is observed in crystallographic studies of 3-bromo-l,8-dimethyl-naphthalene [6]. Indication that there is some distortion of the naphthalene nucleus is obtained from the value of the spin density at the carbon atoms la, 4a, 7a and 10a.…”

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confidence: 79%