Hydrogen bond patterns in aromatic and aliphatic dioximes

Bruton, Eric A.; Brammer, Lee; Pigge, F. Christopher; Aakeröy, Christer B.; Leinen, Destin S.

doi:10.1039/b301045g

Cited by 60 publications

(58 citation statements)

References 68 publications

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“…The mesityl group of (I) and (II) is planar with a maximum deviation from the plane of -0.057Å for C10, 0.015Å for C17 and makes an angle of 87.61 (10) 0 , 78.47 (12) 0 with plane of the benzofuran system (I) and (II) respectively, differing from the values reported between the structures. These differences may be explained by the presence of the different substituents in these compounds.…”

Section: Crystal Structure Of Compoundscontrasting

confidence: 51%

“…Hydrogen-bond patterns in crystalline oximes have been analyzed by Bertolasi et al 9 , followed by a systematic examination of hydrogen-bonding in aromatic and aliphatic oximes by Bruton et al 10 Depending upon the presence of diferent acceptors and donors in oximes, the intermolecular interactions between two or more oximes in the solid-state can be classified into four major categories: Dimers based on O−H···N hydrogen bonds ( (6) motif), catemers directed by O−H···N inter-actions (C(3) chains), catemers governed by O−H···O hydrogen bonds (C(2) chains), and oximes in which the R′ group plays a dominant role by accepting a hydrogen-bond from the oxime moiety (C(6) catemeric chains) 11,12 . In this study, the both molecules are ketoxim structures and the molecule (1) forms a dimeric structure with O-H....N hydrogen bond ( (6) motif).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and X-Ray Structural Characterization of 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanoneoxime and 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanone-O-(2- Phenylacetyl)oxime

Yakalı¹,

Barım²,

Kırılmış³

et al. 2016

J. Chil. Chem. Soc.

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The selected molecules of benzofuran derivatives were synthesized and their structures were studied using the X-ray crystallography and spectroscopic methods. The 1-(5-bromobenzofurane-2-yl)-2-mesitylethanoneoxime (I), C 19 H 18 BrNO 2 , and 1-(5-bromobenzofuran-2-yl)-2-mesitylethanone-O-(2-phenylacetyl) oxime (II), C 27 H 24 BrNO 3 , crystallize in the monoclinic crystal system in space group P2 1 /c with Z = 4 and in the triclinic system in space group P-1 with Z=2, respectively. The both compounds adopt Z conformation. The compound (I) consists of a dimeric arrangement of molecules around an inversion centre formed via a O-H…N intermolecular hydrogen bond linking the molecules -Along the a axis. This centrosymmetric hydrogen-bonded dimers are formed with an (6) ring motif. The compound (II) forms one dimensional infinite chain via C-H···O hydrogen bond along the a axis. Moreover, in the crystal structures of (I), (II) weak C-H..O, C-H…π and π…π interactions serve to organize formation of a two dimensional network. Moreover a short N1-N1 intermolecular contact [2.89 Å] is observed between inversion-related chains in the crystal structure of (I). The two compounds have essentialy similar bond lengths and angles. The prominent discrepancy is observed for the fragment attaching benzofuran ring with mesityl group. Benzofuran groups and other ring groups are almost planar in the crystal structures of (I) and (II).Keywords: Benzofuran derivatives; Oxime derivatives; Crystal structure; X-ray; 2D Network.e-mail addresses:gulyakali@akdeniz.edu.tr ckirilmis@adiyaman.edu.tr INTRODUCTIONBenzofuran contains a ring system obtained by the fusion of a benzene nucleus with a furan ring. The benzofuran ring system, although by no means as common as indole, is incorporated into many natural products and into synthetic pharmaceuticals 1,2 . Oximes are belonging to the imines, with the general formula R 1 R 2 C=NOH, where R 1 is an organic side-chain and R 2 may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. They exist as two geometric stereo isomers: a syn isomer and an anti isomer. Aldoximes, except for aromatic aldoximes, which exist only as anti isomers, and ketoximes can be separated almost completely and obtained as a syn isomer and an anti isomer 3 .The life threatening infections caused by pathogenic fungi have increased during the past two decades and there is need to develop new antifungals with good activity against variety of fungal species. Benzofurans and their derivates have physiological, pharmacological and toxic properties and find application as sedatives, hypnotics, agrochemicals, pharmaceuticals, cosmetics and as the building blocks of optical brighteners [4][5] . Oximes are a very effective antifungal agent so they became a matter of interest 6 . Aryl benzofuryl ketoxime sand their derivatives are highly effective compounds 7 and these some shows excellent anibacterialactivity 8 .Hydrogen-bond patterns in crystalline oximes have been analyzed by Bertolasi et al. 9 , ...

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Section: Crystal Structure Of Compoundscontrasting

confidence: 51%

Section: Introductionmentioning

confidence: 99%

Synthesis and X-Ray Structural Characterization of 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanoneoxime and 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanone-O-(2- Phenylacetyl)oxime

Yakalı¹,

Barım²,

Kırılmış³

et al. 2016

J. Chil. Chem. Soc.

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“…6 However, cyanooximes, 7 where the oxime nitrogen atom is a 25 particularly weak hydrogen-bond acceptor due to the presence of the electron-withdrawing -CN moiety, 8,9 tend to act as a single point hydrogen-bond donors similar to an -OH group. 10 The latter functionality is ubiquitous in biological systems, and is also heavily utilized in applications such as templated covalent 30 synthesis, 11 nonlinear optics 12 and sensors.…”

Section: Scheme 1 the Oxime Moietymentioning

confidence: 99%

Competing hydrogen-bond donors: phenols vs. cyanooximes

et al. 2013

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“…Oximes have an O-H group as hydrogen bond donor; the N and O atoms are potential hydrogen bond acceptors, whereby in most cases bonding to the N atom is preferred [4]. Most of all oximes form hydrogen-bonded dimers in the solid state (graph set R 2 2 (6)), but also trimers [5], tetramers [6] and linear chains [7] are relatively common. Additional flexibility is achieved by the possible E/Z isomerism of the oxime group.…”

Section: Introductionmentioning

confidence: 99%

“…Additional flexibility is achieved by the possible E/Z isomerism of the oxime group. Furthermore, diverse coordination modes including nitrogen-and/or oxygen-coordination to different transition metal atoms are known for oximato-metal species [2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Oxime-substituted NCN-pincer palladium and platinum halide polymers through non-covalent hydrogen bonding (NCN=[C6H2(CH2NMe2)2-2,6]−)

Köcher¹,

Lutz²,

Spek³

et al. 2008

Journal of Organometallic Chemistry

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a b s t r a c tThe oxime-substituted NCN-pincer molecules HON@CH-1-C 6 H 3 (CH 2 NMe 2 ) 2 -3,5 (2a) and HON@CH-4-C 6 H 2 (CH 2 NMe 2 ) 2 -2,6-Br-1 (2b) were accessible by treatment of the benzaldehydes H(O)C-4-C 6 H 3 (CH 2 NMe 2 ) 2 -3,5 (1a) and H(O)C-4-C 6 H 2 (CH 2 NMe 2 ) 2 -2,6-Br-1 (1b) with an excess of hydroxylamine. In the solid state both compounds are forming polymers with intermolecular O-HÁ Á ÁN connectivities between the Me 2 NCH 2 substituents and the oxime entity of further molecules of 2a and 2b, respectively. Characteristic for 2a and 2b is a helically arrangement involving a crystallographic 2 1 screw axis of the HON@CH-1-C 6 H 3 (CH 2 NMe 2 ) 2 -3,5 and HON@CH-4-C 6 H 2 (CH 2 NMe 2 ) 2 -2,6-Br-1 building blocks. The reaction of 2b with equimolar amounts of [Pd 2 (dba) 3 Á CHCl 3 ] (3) (dba = dibenzylidene acetone) or [Pt(tol) 2 (SEt 2 )] 2 (4) (tol = 4-tolyl) gave by an oxidative addition of the C-Br unit to M coordination polymers with a [(HON@CH-4-C 6 H 2 (CH 2 NMe 2 ) 2 -2,6)MBr] repeating unit (5: M = Pd, 6: M = Pt). Complexes 5 and 6 are in the solid state linear hydrogen-bridged polymers with O-HÁ Á ÁBr contacts between the oxime entities and the metal-bonded bromide.

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Hydrogen bond patterns in aromatic and aliphatic dioximes

Cited by 60 publications

References 68 publications

Synthesis and X-Ray Structural Characterization of 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanoneoxime and 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanone-O-(2- Phenylacetyl)oxime

Synthesis and X-Ray Structural Characterization of 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanoneoxime and 1-(5-Bromobenzofuran-2-Yl)-2-Mesitylethanone-O-(2- Phenylacetyl)oxime

Competing hydrogen-bond donors: phenols vs. cyanooximes

Oxime-substituted NCN-pincer palladium and platinum halide polymers through non-covalent hydrogen bonding (NCN=[C6H2(CH2NMe2)2-2,6]−)

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