Structure of 2,2-dichloro-2'-hydroxy-4'-methoxyacetophenone, C9H8Cl2O3

Chattopadhyay, D.; Banerjee, T.; Μazumdar, S. Κ.; Podder, G.

doi:10.1107/s0108270185003651

Acta Crystallogr C

1985

DOI: 10.1107/s0108270185003651

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Structure of 2,2-dichloro-2'-hydroxy-4'-methoxyacetophenone, C9H8Cl2O3

D. Chattopadhyay¹,

T. Banerjee²,

S. Κ. Μazumdar³

et al.

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1986

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Cited by 2 publications

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“…Acetanilide and its various derivatives possess a variety of antifungal, antibacterial, analgesic and anaesthetic activities (Burger, 1960;Banerjee, 1983). The structure of the title compound was analysed as part of our studies on dichloroacetophenones and acetanilides (Chattopadhyay, Banerjee, Mazumdar & Podder, 1985;Haisa, Kashino, Ueno, Shinozaki & Matsuzaki, 1980). Experimental.…”

mentioning

confidence: 99%

Structure of 3'-acetamido-2,2-dichloro-4',5'-dimethylacetophenone

Chattopadhyay¹,

Banerjee²,

Μazumdar³

et al. 1986

Acta Crystallogr C

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mentioning

confidence: 99%

Structure of 3'-acetamido-2,2-dichloro-4',5'-dimethylacetophenone

Chattopadhyay¹,

Banerjee²,

Μazumdar³

et al. 1986

Acta Crystallogr C

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Deuterium and ¹⁸O isotope effects on ¹³C chemical shifts of sterically hindered and/or intramolecularly hydrogen‐bonded o‐hydroxy acyl aromatics

Hansen

Ibsen

Kristensen

et al. 1994

Magnetic Reson in Chemistry

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A series of sterically hindered 0-hydroxy aromatic ketones were synthesized, including benzeae, naphthalene, pbeoanthene and pyrene derivatives. Deuterium isotope effects on the 13C chemical shifts of 2-hydroxy-l-acenaphthone and other sterically hindered, intramolcularly hydrogen-bonded aromatic ketones (OH exchanged) are shown to he M U S U~~. The two-bond isotope effects are very large. Likewise are the istope eff& on C-0, C-1, C-3 a d C-4 carbon resonances and some show unltsual signs. These unusual effects 8re e x p l a i d by a higher degree of twist in the deuterio than the protio compound. Steric isotope effects are also observed on OH chemical shifts of sterically hindered o-hydroxy acetyl aromatic compounds deuteriated at the methyl group. These isotope effeets show non-additivity. For one-bond isotope effects, IA"C ( l a 0), hydrogen bonding leads to a decrease, whereas twisting of the carbonyl group leads to an increase. Two hydrogen bonds to the same acceptor has a reduced cumulative effect. Data for sterically hindered, hydrogen-bonded compounds are found to fall outside the correlation between 6(''O) and 1A13C(180).KEY WORDS NMR NMR Isotope effects on "C chemical shifts Deuterium isotope effects "0 isotope effects Intramolecular hydrogen bonding Steric strain Hydrogen bond strength

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Structure of 2,2-dichloro-2'-hydroxy-4'-methoxyacetophenone, C9H8Cl2O3

Cited by 2 publications

References 6 publications

Structure of 3'-acetamido-2,2-dichloro-4',5'-dimethylacetophenone

Structure of 3'-acetamido-2,2-dichloro-4',5'-dimethylacetophenone

Deuterium and ¹⁸O isotope effects on ¹³C chemical shifts of sterically hindered and/or intramolecularly hydrogen‐bonded o‐hydroxy acyl aromatics

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Structure of 2,2-dichloro-2'-hydroxy-4'-methoxyacetophenone, C9H8Cl2O3

Cited by 2 publications

References 6 publications

Structure of 3'-acetamido-2,2-dichloro-4',5'-dimethylacetophenone

Structure of 3'-acetamido-2,2-dichloro-4',5'-dimethylacetophenone

Deuterium and 18O isotope effects on 13C chemical shifts of sterically hindered and/or intramolecularly hydrogen‐bonded o‐hydroxy acyl aromatics

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Deuterium and ¹⁸O isotope effects on ¹³C chemical shifts of sterically hindered and/or intramolecularly hydrogen‐bonded o‐hydroxy acyl aromatics