Proton spin–spin coupling constants and intramolecular hydrogen bonding in bromine derivatives of 1,3-dihydroxybenzene
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The conformational preferences in CCl4 solution at 32 °C of the hydroxyl groups in bromine derivatives of 1,3-dihydroxybenzene are deduced from the long-range spin–spin coupling constants between hydroxyl protons and ring protons over five bonds. Two hydroxyl groups hydrogen bond to the same bromine substituent in 2-bromo-1,3-dihydroxybenzene but prefer to hydrogen bond to different bromine substituents when available, as in 2,4-dibromo-1,3-dihydroxybenzene. When the OH groups can each choose between two ortho bromine atoms, as in 2,4,6-tribromoresorcinol, they apparently do so in a very nearly statistical manner except that they avoid hydrogen bonding to the common bromine atom.
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1983 ◽
Vol 4
(3)
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pp. 428-437
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2005 ◽
Vol 109
(47)
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pp. 10759-10769
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1984 ◽
Vol 25
(3)
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pp. 379-384
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1976 ◽
Vol 61
(3)
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pp. 479-480
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1969 ◽
Vol 4
(5-6)
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pp. 445-457
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