Category: CH/n hydrogen bond (mostly CH/O and CH/N)

A comprehensive review on these interactions appears in Chapter 2 in The Weak Hydrogen Bond in Structural Chemistry and Biology, by G. R. Desiraju and T. Steiner, Oxford Univ. Press, 1999.

O. Takahashi et al., Chem. Phys. Lett. 2007, 440, 64-69: Origin of the gauche preference of n-propyl halides and related molecules investigated by ab initio MO calculations. Importance of the CH/n hydrogen bond.

O. Takahashi et al., Carbohydr. Res. 2007, 342, 1202-1209: The anomeric effect revisited. A possible role of the CH/n hydrogen bond.

J. Althoff et al., CrystEngComm 2006, 8, 662-665: Can a single C-H/F-C bond make a difference? Assesing the H/F bond strenth from 2-D 1H19F CP/MAS NMR.

T. Dorn et al., CrystEngComm, 2005, 7, 633-641: Hydrogen-bonding, pi-stacking, and Cl- -anion-pi interactions of linear bipyridinium cations with phosphate, chloride and [CoCl4]2- anions.

C. G. Pozzi et al., J. Molec. Struct. 2005, 753, 173-181: Close shell interactions in 3-ethoxycarbonyl-4-hydroxy-6-methoxymethyleneoxy-1-methyl-2-quinolone: 100 K single crystal neutron diffraction study and ab initio calculations.

G. R. Desiraju, Chem. Commun. 2005, 2995-3001: C-H...O and other weak hydrogen bonds. From crystal engineering to virtual screening. [Review]

I. Yu et al., Bull. Chem. Soc. Jpn. 2003, 76, 529-539: Molecular modeling of the solvent of DMSO around cellulose triacetate.

K. Biradha, CrystEngComm 2003, 5, 374-384: Crystal engineering: from weak hydrogen bonds to co-ordination bonds. [Review]

R. Boese et al., Angew. Chem. Int. Ed. 2003, 42, 1961-1963: Cocrystallization with acetylene: Molecular complexes with acetone and dimethyl sulfoxide.

K. Praveen et al., CrystEngComm, 2003, 5, 87-92: CH/O hydrogen bonds in molecular complexes of 1,3,5-trinitrobenzene with some N-heterocycles.

O. Takahashi et al., Bull. Chem. Soc. Jpn. 2003, 76, 369-374: General preference for alkyl/phenyl folded conformations. Relevance of the CH/pi and CH/O interactions to stereochemistry as evidenced by ab Initio MO calculations. [See page 'Our papers' for Abstract]

O. Takahashi et al., Bull. Chem. Soc. Jpn. 2002, 75, 1777-1783: The conformation of 2-phenylpropionaldehyde and alkyl 1-phenylethyl ketones as evidenced by ab initio calculations. Relevance of the CH/pi and CH/O interactions in stereochemistry. [See page 'Our papers' for Abstract]

R. Cini et al., Inorg. Chim. Acta 2002, 339, 89-103: Synthesis, electrochemical studies, density functional analysis and X-ray structures of trans,cis,cis-[RuCl2(N-methylimidazole)2(SbPh3)2] and trans,cis,cis-[RuCl2(4-methylpyrimidine)2(SbPh3)2]. The role of CH-N and CH-Cl interactions in pyrimidine pairings and in tuning the angular approach of imidazole residues to metals.

R. Zhao et al., Tetrahedron 2002, 58, 10225-10231: Novel organic crystals with redﾐviolet metallic luster: 1-aryl-2-(2-thienyl)-5-[5-(tricyanoethenyl)-2-thienyl]pyrrole derivatives bearing a heteroatom combined methyl substituent.

S. F. Alshahateet et al., CrystEngComm 2002, 4, 585-590: Interlocking molecular grid lattices involving weak assembly forces.

M. Felloni et al., CrystEngComm 2002, 4, 483-495: Hydrogen-bonding interactions between linear bipyridinium cations and nitrate anions.

A. Nangia, CrystEngComm 2002, 17, 1-9: Database research in crystal engineering. [REVIEW]

M. P. M. Marques et al., J. Phys. Chem. A, 2001, 105, 5292-5297: Evidence of C-H/O hydrogen bonds in liquid 4-ethoxybenzaldehyde by NMR and vibrational spectroscopies.

Y. Sasanuma et al., J. Phys. Chem. A, 2001, 105, 3277-3283: Carbon-13 NMR Chemical shifts of dimeric model compounds of poly(propylene oxide): A proof of existence of the CH-O attraction.

S. Tsuzuki et al., J. Chem. Soc., Perkin Trans. 2 2001, 1951-1955: Effects of CH/O and CH/pi interactions on the conformational preference of a crownophane core unit.

S. Tamagaki, K. Batoh, J. Chem. Soc., Perkin Trans. 2 2001, 1389-1393: Remarkable selectivity of per-O-methylated tricationic 6A,6C,6E-tripyridino-6A,6C,6E-trideoxy-alpha-cyclodextrin for basic anions over non-basic anions. {CH/anion interaction]

M. Hartmann et al., J. Phys. Chem. A, 2001, 105, 4470-4479: C-H/X hydrogen bonds of acetylene, ethylene, and ethane with first- and second-row hydrides.

R. Cini et al., Inorg. Chem. 2000, 39, 5874-5878: Supramolecular aggregates of complex cations via unusual purine-purine base pairing in new organorhodium(III) compounds containing the antileukemic drug purine-6-thione.

Y. Yoshitake et al., Tetrahedron Lett., 2000, 41, 4395-4400: Effect of >C=O---H-Ar interaction on endo/exo selectivity in the Diels-Alder reaction of phenyl-substituted cyclopentadienones.

M. Hartmann, L. Radom, J. Phys. Chem. A, 2000, 104, 968-973: The acetylene-ammonia dimer as a prototypical CH-N hydrogen bonded system: An assessment of theoretical procedures.

V. R. Thalladi et al., New J. Chem. 2000, 463-470: C-H group acidity and the nature of CH-N interactions: Crystal structural analysis of pyrazine and methyl substituted pyrazines.

J. van de Bovencamp et al., J. Phys. Chem. A, 1999, 103, 2784-2792: Combined ab initio computational and statistical investigation of a model CH-O hydrogen bonded dimer as occurring in 1,4-benzoquinone.

Y. Gu et al., J. Am. Chem. Soc. 1999, 121, 9411-9422: Fundamental properties of the CH-O interaction: Is it a true hydrogen bond?

K. N. Houk et al., J. Am. Chem. Soc. 1999, 121, 1479-1487: CH-O interactions as a control element in supramolecular complexes: Experimental and theoretical evaluation of receptor affinities for the binding of bipyridinium-based guests by catenated hosts.

J. M. A. Robinson et al., Chem. Commun. 1999, 329-330: Predictable solid state structures incorporating the C(triple bond)CH-O2N supramolecular synthon.

F. Blockhuys et al., J. Mol. Struct. 1999, 485-486, 87-96: Cis/trans isomerizations in 1,2-bis(2-thienyl)ethene derivatives: a joint experimental and computational approach.

R. K. O. Sigel et al., J. Am. Chem. Soc. 1998, 120, 12000-12007: Metalated nucleobase quartets: Dimerization of a metal-modified guanine, cytosine pair of trans-(NH3)2Pt(II) and formation of CH/N hydrogen bonds.

V. R. Thalladi et al., J. Am. Chem. Soc. 1998, 120, 8702-8710: CH/F interactions in the crystal structures of some fluorobenzenes.

T. Steiner, New J. Chem. 1998, 22, 1099-1103: Donor and acceptor strengths in CH-O hydrogen bonds quantified from crystallographic data of small solvent molecules. [REVIEW]

Nangia, A., Desiraju, G. R., Acta Cryst., Sect. A. 1998, 54, 934-944: Supramolecular structures: Reason and imagination. [REVIEW]

T. Steiner, G. R. Desiraju, Chem. Commun. 1998, 891-892: Distinction between the weak hydrogen bond and the van der Waals interaction.

P. Chakrabarti, S. Chakrabarti, J. Mol. Biol 1998, 284, 867-873: C-H/O hydrogen bond involving proline residues in alpha helices.

M. Mascal, Chem. Commun. 1998, 303-304: Statistical analysis of CH-N hydrogen bonds in the solid state: there are real precedents.

S. Kumar et al., J. Molec. Struct. 1998, 471, 251-255: Crystal structure of N-cyano-N-prop-2-ynyl-aniline and structural data on C(triple bond)CH-N hydrogen bonds.

B. M. Kariuki et al., J. Am. Chem. Soc. 1997, 119, 12679-12680: A triphenylphosphine oxide-water aggregate facilitates an exceptionally short CH-O hydrogen bond.

H. Yoshida et al., Chem. Commun. 1997, 2213-2214: Infrared spectroscopic evidence for an intramolecular 1,5-CH...O attractive interaction in 1-methoxy-2-(methylthio)ethane.

F. A. Cotton et al., Chem. Commun. 1997, 1673-1674: The crystal packing of bis(2,2'-dipyridylamido)cobalt(II), Co(dpa)2, is stabilized by CH-N bonds: are there any real precedents?

T. Steiner, Chem. Commun. 1997, 727-734: Unrolling the hydrogen bond properties of CH-O interactions. [REVIEW]

G. F. Fabiola et al., Acta Cryst., Sect. A. 1997, 53, 316-320: CH-O hydrogen bond in betha-sheets.

T. Steiner, Chem. Commun. 1997, 191-192: Spectroscopic evidence for cooperativity effects involving CH-O hydrogen bonds: crystalline mestranol.

J. J. Novoa, F. Mota, Chem. Phys. Lett. 1997, 266, 23-30: Substituent effects in intermolecular C(sp3)-H...O(sp3) contacts: How strong can a C(sp3)-H...O(sp3) hydrogen bond be?

M. Iwaoka et al., Bull. Chem. Soc. Jpn. 1996, 69, 1825-1828: Deuterium-induced isotope effects of a C-HﾉSe hydrogen bond on the IR and NMR spectra of 6H,12H-dibenzo[b,f][1,5]diselenocin.

M. Mascal et al., Tetrahedron Lett. 1996, 37, 3505-3506: Molecular structure of the s-triazine-Br2 complex

V. R. Pedireddi et al, J. Chem. Soc., Chem. Commun. 1996, 997-1002: Creation of crystalline supramolecular assemblies using a C–H⋯O/O–H⋯N pair-wise hydrogen bond coupling.

J. Bella, H. M. Berman, J. Mol. Biol. 1996, 264, 734-742: Crystallographic evidence for CH...O=C hydrogen bonds in a collagen triple helix.

H. Yoshida et al., Chem. Lett., 1996, 637-638: Conformational stability of 1,2-dimethoxyethane in the gas phase studied by infrared spectroscopy: Importance of an intramolecular 1,5-CH/O interaction.

G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449: The CH-O hydrogen bond: Structural implications and supramolecular design [REVIEW].

J. L. Adcock, H. Zhang, J. Org. Chem. 1995, 60, 1999-2002: Polarized C-H groups as novel hydrogen-bond donors in hydryl-F-alkyl esters: Unequivocal examples for the "Pinchas effect".

Z. S. Derewenda et al., J. Mol. Biol. 1995, 252, 248-262: The occurrence of CH-O hydrogen bonds in proteins.

G. A. Leonard et al., Acta Crystallogr. Sect D 1995, 51, 136-139: Do CH-O hydrogen bonds contribute to the stability of nucleic acid base pairs?

T. Steiner, Acta Cryst., Sect D. 1995, 51, 93-97: Water molecules which apparently accept no hydrogen bonds are systematically involved in CH-O interactions.

M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1994, 116, 4463-4464: First observation of a CH...Se "hydrogen bond".

D. S. Reddy et al., J. Chem. Soc., Chem. Commun. 1994, 1457-1458: Organic alloys: diamondoid networks in crystalline complexes of 1,3,5,7-tetrabromoadamantane, hexamethylenetetramine and carbon tetrabromide.

T. Steiner, W. Saenger, J. Am. Chem. Soc. 1993, 115, 4540-4547: Role of CH-O hydrogen bonds in the coordination of water molecules. Analysis of neutron diffraction data.

C. Avendano et al., J. Chem. Soc., Perkin Trans. 2 1993, 1547-1555: The problem of the existence of C(Ar)-H/N intramolecular hydrogen bonds in a family of 9-azaphenyl-9H-carbazoles.

S. Tsuzuki et al., J. Phys. Chem., 1993, 97, 1346-1350: Conformational analysis of 1,2-dimethoxyethane by ab initio molecular orbital and molecular mechanics calculations: stabilization of the TGG' rotamer by the 1,5-CH3/O nonbonding attractive interaction.

D. S. Reddy et al., J. Chem. Soc., Chem. Commun. 1993, 663-664: CH-N mediated hexagonal network in the crystal structure of the 1:1 molecular complex 1,3,5-tricyanolbenzene-hexamethylbenzene.

T. Steiner, W. Saenger, J. Am. Chem. Soc. 1992, 114, 10146-10154: Geometry of CH-O hydrogen bonds in carbohydrate crystal structures. Analysis of neutron diffraction data.

T. Suzuki et al., J. Org. Chem. 1992, 57, 6744-6748: Molecular recognition through CH-O hydrogen bonding in charge-transfer crystals: Highly selective complexation of 2,4,7-trinitrofluorenone with 2,6-dimethylnaphthalene.

V. R. Pedireddi, G. R. Desiraju, J. Chem. Soc., Chem. Commun. 1992, 988-990: A crystallographic scale of carbon acidity.

H. Yoshida et al., Chem. Phys. Lett., 1992, 196, 601-606: Importance of an intramolecular 1,5-CH/O interaction and intramolecular interactions as factors determining conformational equilibria in 1,2-dimethoxyethane: a matrix-isolation infrared spectroscopy.

G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296: The CH-O hydrogen bond in crystals: What is it? [REVIEW].

G. R. Desiraju, J. Chem. Soc., Chem. Commun. 1990, 454-455: Strength and linearity of CH-O bonds in molecular crystals: A database study of some terminal alkynes.

P. Seiler, J. D. Dunitz, Helv. Chim. Acta 1989, 1125-1135: An eclipsed C(sp3)-CH3 bond in a crystalline hydrated tricyclic orthoamide: Evidence for CH-O hydrogen bonds.

G. R. Desiraju, J. Chem. Soc., Chem. Commun. 1989, 179-180: Distance dependence of CH-O interactions in some chloroalkyl compounds.

H. Satonaka et al., Bull. Chem. Soc. Jpn. 1988, 61, 2031-2037: NMR spectroscopic study of the conformational preference of methoxycarbonyl and methyl substituted thiophenecarbaldehydes. Possibility of a hydrogen-bond-like interaction between formyl C-H and the ester carbonyl group.

Y. Tamura et al., Bull. Chem. Soc. Jpn. 1987, 60, 1781-1788: CH3-O hydrogen bond. Implications of its presence from the substituent effects on the populations of rotamers in 4-substituted 9-ethyl-1-methoxytriptycenes and 9-(substituted phenoxymethyl)-1,4-dimethyltriptycenes.

G. R. Desiraju, J. A. R. P. Sarma, J. Chem. Soc., Perkin Trans. 2. 1987, 1195-1202: CH-O interactions and the adoption of 4 A short-axis crystal structures by oxygenated aromatic compounds.

G. R. Desiraju, B. N. Murty, Chem. Phys. Lett. 1987, 139, 360-361: Correlation between crystallographic and spectroscopic properties fro CH-O bonds in terminal acetylenes.

Z. Berkovitch-Yellin, L. Leiserowitz, Acta Crystallogr., Sect. B 1984, 40, 159-165: The role played by C-H/O and C-H/N interactions in determining molecular packing and conformation.

E. Weber et al., J. Chem. Soc., Chem. Commun. 1986, 467-469: Enclave inclusion of nitromethane by a new crown host. X-Ray crystal structure of the inclusion complex and host selectivity properties.

M. Meot-Ner, C. A. Deakyne, J. Am. Chem. Soc. 1985, 107, 469-474: Unconventional Ionic hydrogen bonds. 1. CH-X complexes of quaternary ions with n- and pi-donors.

R. Taylor, O. Kennard, J. Am. Chem. Soc. 1982, 104, 5063-5070: Crystallographic evidence for the existence of CH-O, CH-N, and CH-Cl hydrogen bonds.

S. Zushi et al., Bull. Chem. Soc. Jpn. 1980, 53, 3631-3640: The conformations of 2-phenylpropionaldehyde and some aliphatic ketones. The possible importance of the CH/pi and CH/n interactions in determining the molecular geometry of a mobile system.

F. G. Canepa et al., Nature 1966, 210, 907-909: Structure of acetylcholine and other substrates of cholinergic systems.

S. Pinchas, J. Phys. Chem. 1963, 67, 1862-1865: Intramolecular hydrogen bonding in o-nitrobenzaldehyde and related compounds.

D. J. Sutor, J. Chem. Soc. 1963, 1105-1110: Evidence for the existence of CH-O hydrogen bonds in crystals.

A. Allerhand, P. von R. Schleyer, J. Am. Chem. Soc. 1963, 85, 1715-1723: A survey of C-H groups as proton donors in hydrogen bonding.

D. J. Sutor, Nature 1962, 195, 68-69: The CH-O hydrogen bond in crystals.

J. C. D. Brand et al., J. Chem. Soc. 1960, 2526-2533: The ethynyl-hydrogen bond. Part I. Association in ether solution.

G. C. Pimentel, A. L. McClellan, The Hydrogen Bond, W. H. Freeman, San Francisco, 1960, 197: Do C-H groups form hydrogen bonds? [BOOK].

S. Pinchas, Anal. Chem. 1957, 279, 334-339: Infrared absorption of aldehydic C-H group: ortho-substituted benzaldehydes.

G. J. Korinek, W. G. Schneider, Can. J. Chem. 1957, 35, 1157-1163: On the proton magnetic resonance shift due to hydrogen bonding.

S. Pinchas, Anal. Chem. 1955, 27, 2-6: Infrared absorption of the aldehydic C-H group.