INTRAMOLECULAR HYDROGEN BONDING TO π-ELECTRONS IN ortho-SUBSTITUTED PHENOLS

Beckering, Willis.

doi:10.1021/j100820a004

Cited by 17 publications

(9 citation statements)

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“…Nevertheless, its distribution is qualitatively similar to that for the latter distances and thus corroborative. Convertingregression equations to differences one obtains 6 , : …”

Section: Directionality and Length Of The X-h(x) N Bond: Crystalsmentioning

confidence: 99%

“…The authors concluded that the cation undergoes a complicated composite motion: the complete ion jumps about its N-H axis (E, = 20.1 (20) 6. Mean values of the X...x, and H(X) ... x, distances (A) and (0.06 A2 < Uii < 1.14 A2, Table A), they are quite satisfactorily "bond" angles w (deg) in compounds of Table 1 accounted for as arising from a rigid-body motion (RBM) of the cation: R(U,,.)…”

Section: Mtb and 3etbmentioning

confidence: 99%

“…P2,la (7): h01, h odd; OM), k odd; hOO, h odd. P2,ln (6,8,10): h01, h+l odd; OM), k odd; hOO, h odd; 001,l odd.…”

Section: Structure Determinationunclassified

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Crystal chemistry of tetraradial species. Part 4. Hydrogen bonding to aromatic π systems: crystal structures of fifteen tetraphenylborates with organic ammonium cations

Bakshi¹,

Linden²,

Vincent³

et al. 1994

Can. J. Chem.

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The aim of this investigation is to provide a classification and examples of N—H …π (and also O—H …π) bonds to the aromatic π systems in organic ammonium tetraphenylborates that would serve as reference for X—H …π(arene) bonds in general. To this end the crystal structures of the tetraphenylborates of the following cations have been determined: Me3NH+, Et3NH+, quinuclidinium, DabcoH+, Et(iso-Pr)2NH+ (monohydrate), (Ph3B)NH[—(CH2)2—]2NHMe+ (Me2CO solvate), Me2NH2+ (MeCN and Et2CO solvates), Et2NH2+, (iso-Pr)2NH2+, azoniacycloheptane, guanidinium (monohydrate), MeNH3+, EtNH3+, and 1-adamantammonium (monohydrate). These structures contain a variety of normal, bifurcated, and trifurcated N—H …π bonds as well as normal O—H …π bonds to the phenyl groups of the anion. The X—H …π bonds will form whenever opportunity arises, even though the result may be unfavourable bonding geometry. Branched bonds and orientational disorder represent compromise solutions in situations where the H(X) hydrogens are presented with competing phenyl acceptors or where the general organization of the crystal structure offers unfavourable bonding conditions to these hydrogens. The distributions of the distances from X or H(X) to the centre of the phenyl-ring skeleton are analyzed in detail, as are also those of the mean X … C and H(X)… C distances to the ring carbons.

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“…Nevertheless, its distribution is qualitatively similar to that for the latter distances and thus corroborative. Convertingregression equations to differences one obtains 6 , : …”

Section: Directionality and Length Of The X-h(x) N Bond: Crystalsmentioning

confidence: 99%

Section: Mtb and 3etbmentioning

confidence: 99%

See 1 more Smart Citation

Crystal chemistry of tetraradial species. Part 4. Hydrogen bonding to aromatic π systems: crystal structures of fifteen tetraphenylborates with organic ammonium cations

Bakshi¹,

Linden²,

Vincent³

et al. 1994

Can. J. Chem.

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show abstract

“…Comparable results were obtained by Beckering [31], and by Kuhn [32]. Baker and Shulgin [30] studied o-allylphenol, 0propenylphenol and compounds with more heavily substituted double bonds.…”

Section: (E) Ternary Systemsmentioning

confidence: 75%

Associated XH Frequencies, the Hydrogen Bond

Bellamy¹

1980

The Infrared Spectra of Complex Molecules

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“…The o.o'-biphenyldioxydiacetamide (2 a) is synthesized via the same route except that two equivalents o f the corresponding chloroacetamide as well as potassium f-butoxide were used and a longer reaction time was applied [16,17]. Table IV gives the yield, the method of purification and the melting point of the various compounds.…”

Section: Synthetic Proceduresmentioning

confidence: 99%