Geometrical substituent parameters for benzene derivatives: inductive and resonance effects

Domenicano, Aldo; Murray‐Rust, Peter

doi:10.1016/s0040-4039(01)93699-8

Cited by 298 publications

(177 citation statements)

References 6 publications

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“…The intraannular bond angles within the phenyl rings reflect the nature of the substituents, generally in accordance with the findings of Domenicano and Murray-Rust [12] and Exner and Böhm [13].…”

Section: Resultssupporting

confidence: 88%

Isomorphism in Two (E)-1-(4-Halophenyl)-N-[1-(4-Methylphenyl)-1H-Imidazol-4-yl]Methanimines (Halide = Cl, Br)

et al. 2012

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The crystal structures of two imidazole-4-imines, (E)-1-(4-chlorophenyl)-N-[1-(4-methylphenyl)-1H-imidazol-4-yl]methanimine (1, C 17 H 14 ClN 3 ), and (E)-1-(4-bromophenyl)-N-[1-(4-methylphenyl)-1H-imidazol-4-yl] methanimine, (2, C 17 H 14 BrN 3 ), are isomorphous, the isostructurality index is 99.4 %. Both compounds crystallize in the triclinic space group P-1 with unit cell parameters at 100(1) K as follows: for (1), a = 7.9767(5) Å , b = 10.9517(7) Å , c = 16.6753(12) Å , a = 80.522(6)°, b = 87.046(6)°, c = 89.207(5)°, and for (2), a = 8.0720(7) Å , b = 10.9334(10) Å , c = 16.8433(13) Å , a = 81.161(7)°, b = 86.605(7)°, c = 89.505(7)°. The structures contain two symmetry-independent but conformationally similar molecules in the asymmetric unit (Z' = 2). In both compounds the overall twist of the molecule, defined as the dihedral angle between the terminal phenyl ring planes is significant, around 56°. The crystal packing is determined mainly be weak specific intermolecular interactions: the C-HÁÁÁN hydrogen bonds connect molecules into infinite chains, and the chains are linked via C-HÁÁÁX hydrogen bonds and by p-p interactions. This study illustrates the significant role of the weak interactions, which-in spite of their weakness-can robustly repeat in the crystal structures of similar compounds.

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Section: Resultssupporting

confidence: 88%

Isomorphism in Two (E)-1-(4-Halophenyl)-N-[1-(4-Methylphenyl)-1H-Imidazol-4-yl]Methanimines (Halide = Cl, Br)

et al. 2012

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“…Compared with an unsubstituted benzo part (Meurisse, Blaton, Peeters & De Ranter, 1992), the deformations of the internal angles agree quite well with the values given by Domenicano & Murray-Rust (1979). Bond lengths and remaining angles show little deviation from values found in other compounds of the series (Peeters, Blaton, Meurisse & De Ranter, 1994a,b (A, o) …”

Section: Commentsupporting

confidence: 82%

2-[(3-Furoyl)aminomethyl]-1,7-dimethyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-4-ium Chloride

Blaton¹,

Peeters²,

Meurisse³

et al. 1996

Acta Crystallogr C

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“…In the 5,7-disubstituted derivatives the influence of the substituents should be additive and even though this additivity is not perfect, a trend is apparent. The differences in the bond angles of (II), (III) and (V) compared with QD itself are listed in Table 5, together with values obtained from the analysis of Domenicano & Murray-Rust (1979). In (II) there are two symmetrically independent molecules in the asymmetric part of the unit cell.…”

Section: Molecular Structuresmentioning

confidence: 99%

Hydrogen-bond patterns in 1,4-dihydro-2,3-quinoxalinediones: ligands for the glycine modulatory site on the NMDA receptor

Kubicki¹,

Kindopp²,

Capparelli³

et al. 1996

Acta Crystallogr Sect B

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The crystal structures of five 1,4-dihydro-2,3-quinoxalinediones, antagonists of the NMDA modulatory glycine binding site on the excitary amino acid (EAA) receptor complex, have been determined: (I) 6,7-dinitro-l,4-dihydro-2,3-quinoxalinedione (DNQX); (II) 5,7-dinitro-1,4-dihydro-2,3-quinoxalinedione (MNQX); (III) 6-nitro-1,4-dihydro-2,3-quinoxalinedione hydrate; (IV) 6,7-dichloro-l,4-dihydro-2,3-quinoxalinedione; (V) 5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione dimethylformamide. The crystal structure of the most active compound (II) contains a unique intramolecular N--H...O(NO2) hydrogen bond, which may be important for activity, as semiempirical calculations show that this bond is stable over a wide range of dihedral angles between the planes of the molecule and of the nitro group. In the other compounds the intermolecular hydrogen bonds connect molecules into three-dimensional networks. In compounds (I), (III) and (IV) headto-tail :r-stacking is found between molecules connected by a center of symmetry. The geometries of the hydrogen-bonded --NH--C--O fragments show evidence of zr-cooperativity or resonance-assisted hydrogen bonding. Graph-set analysis of the hydrogenbond patterns of quinoxalinedione derivatives shows a tendency to form two types of hydrogen-bonding motifs: a centrosymmetric dimeric ring and an infinite chain. Even though this pattern may be modified by the presence of additional hydrogen-bond acceptors and/or donors, as well as by solvent molecules, general similarities have been found. Comparison of all quinoxalinedione structures suggests that the hydrogen-bonding pattern necessary for the biological activity at the glycine binding site contains one donor and two acceptors.

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Geometrical substituent parameters for benzene derivatives: inductive and resonance effects

Cited by 298 publications

References 6 publications

Isomorphism in Two (E)-1-(4-Halophenyl)-N-[1-(4-Methylphenyl)-1H-Imidazol-4-yl]Methanimines (Halide = Cl, Br)

Isomorphism in Two (E)-1-(4-Halophenyl)-N-[1-(4-Methylphenyl)-1H-Imidazol-4-yl]Methanimines (Halide = Cl, Br)

2-[(3-Furoyl)aminomethyl]-1,7-dimethyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-4-ium Chloride

Hydrogen-bond patterns in 1,4-dihydro-2,3-quinoxalinediones: ligands for the glycine modulatory site on the NMDA receptor

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