Double Substitution Leads to A Highly PolymorphicSystem in 5-Methyl-2-m-tolylamino-benzoic Acid

CrystEngComm ◽  
2021 ◽  
Author(s):  
Yunping Zhoujin ◽  
Yang Tao ◽  
Panpan Zhou ◽  
Sean R. Parkin ◽  
Tonglei Li ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Aromatic Rings ◽  
Polymorphic Behavior ◽  
Methyl Group ◽  
Double Substitution

By instilling methyl group(s) to either or both aromatic rings of fenamic acid (FA), three FA derivatives (1-3) were synthesized to investigate the effect on the polymorphic behavior of these...

The biosynthesis of ephedrine

1989 ◽  
Vol 67 (6) ◽  
pp. 998-1009 ◽  
Author(s):  
Gunnar Grue-Sørensen ◽  
Ian D. Spenser
Keyword(s):  
Carbon Atom ◽  
Benzoic Acid ◽  
Pyruvic Acid ◽  
Nmr Spectra ◽  
Carbon Skeleton ◽  
Resonance Spectroscopy ◽  
Methyl Group ◽  
Acid Incorporation ◽  
Group A ◽  
C Nmr

It is shown by 13C nuclear magnetic resonance spectroscopy that the labelled C2 fragment of [2,3-13C2]pyruvic acid is transferred intact into the C-methyl group and the adjacent carbon atom of the Ephedra alkaloids, norephedrine, ephedrine, norpseudoephedrine, and pseudoephedrine, in growing plants of Ephedragerardiana. This finding serves to identify pyruvate as the elusive precursor of the aliphatic C2 terminus of the skeleton of the alkaloids. In earlier experiments with C-labelled substrates, label from [3-14C]pyruvic acid was incorporated mainly, but not exclusively, into the C-methyl group of ephedrine, and label from [2-14C]pyruvate was incorporated similarly into the carbon atom adjacent to the C-methyl group. A C6–C1 unit related to benzaldehyde or benzoic acid has long been known to generate the benzylic fragment of the carbon skeleton of the Ephedra alkaloids. It is likely that the carbon skeleton of ephedrine is generated from pyruvate and either benzaldehyde or benzoic acid, by a reaction analogous to the formation of acetoin or diacetyl from pyruvate and acetaldehyde or acetic acid, respectively. Keywords: biosynthesis of ephedrine, Ephedra alkaloids, 13C NMR spectra, ephedrine, biosynthesis of pyruvic acid, incorporation into ephedrine13C NMR spectra.

scholarly journals (E)-2-Methyl-6-{[(5-methylpyridin-2-yl)imino]methyl}phenol

IUCrData ◽  
2017 ◽  
Vol 2 (1) ◽  
Author(s):  
Md. Azharul Arafath ◽  
Farook Adam ◽  
Mohd. R. Razali
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Zigzag Chain ◽  
Aromatic Rings ◽  
Methyl Group ◽  
Compound C

In the title compound, C14H14N2O, the dihedral angle between the aromatic rings is 5.54 (9)°. The conformation is reinforced by an intramolecular O—H...N hydrogen bond, which closes anS(6) ring. The pyridine N atom and methyl group lie to opposite sides of the molecule. In the crystal, the molecules are linked into a zigzag chain propagating in [0-11] by weak C—H...O hydrogen bonds.

scholarly journals Methyl (E)-2-({2-[(E)-(hydroxyimino)methyl]phenoxy}methyl)-3-(4-methylphenyl)acrylate

2012 ◽  
Vol 68 (6) ◽  
pp. o1617-o1617
Author(s):  
G. Ganesh ◽  
J. Srinivasan ◽  
E. Govindan ◽  
M. Bakthadoss ◽  
A. SubbiahPandi
Keyword(s):  
Double Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Crystal Packing ◽  
Aromatic Rings ◽  
Methyl Group ◽  
Compound C ◽  
Benzene Rings ◽  
The Mean ◽  
Centrosymmetric Dimers

In the title compound, C19H19NO4, the dihedral angle between the mean planes through the benzene rings is 82.18 (7)°. The C=N double bond is trans-configured. The molecules are linked into centrosymmetric dimers via pairs of O—H...N hydrogen bonds with the motif R 2 2(6). The crystal packing also features C—H...O interactions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51 (4):0.49 (4)].

scholarly journals Relative substituent orientation in the structure ofcis-3-chloro-1,3-dimethyl-N-(4-nitrophenyl)-2-oxocyclopentane-1-carboxamide

2014 ◽  
Vol 70 (9) ◽  
pp. 121-123
Author(s):  
Matthias Zeller ◽  
Jonas Warneke ◽  
Vladimir Azov
Keyword(s):  
Hydrogen Bond ◽  
Crystal Packing ◽  
Membered Ring ◽  
Amide Group ◽  
Aromatic Rings ◽  
Methyl Group ◽  
Compound C ◽  
The Mean ◽  
Graph Set ◽  
Intramolecular Hydrogen

The structure of the title compound, C14H15ClN2O4, prepared by reaction of a methacryloyl dimer with nitroaniline, was determined to establish the relative substituent orientation on the cyclopentanone ring. In agreement with an earlier proposed reaction mechanism, the amide group and the methyl group adjacent to the chloro substituent adopt equatorial positions and relativecisorientation, whereas the Cl substituent itself and the methyl group adjacent to the amide have axial orientations relative to the mean plane of the five-membered ring. The conformation of the molecule is stabilized by one classical N—H...O (2.18 Å) and one non-classical C—H...O (2.23 Å) hydrogen bond, each possessing anS(6) graph-set motif. The crystal packing is defined by several non-classical intramolecular hydrogen bonds, as well as by partial stacking of the aromatic rings.

scholarly journals N-[2-(Methylsulfanyl)phenyl]-2-sulfanylbenzamide

2012 ◽  
Vol 68 (8) ◽  
pp. o2400-o2400
Author(s):  
Chang-Chih Hsieh ◽  
Hon Man Lee ◽  
Yih-Chern Horng
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Intramolecular Hydrogen Bond ◽  
Title Compound ◽  
Aromatic Rings ◽  
Intermolecular Hydrogen Bonds ◽  
Methyl Group ◽  
Interplanar Angle ◽  
Compound C ◽  
Intramolecular Hydrogen

In the title compound, C14H13NOS2, the S atom with the methyl group is involved in an intramolecular hydrogen bond with the amido H atom. In the crystal, the sulfanyl H atoms form intermolecular hydrogen bonds with the O atoms, connecting the molecules into zigzag chains along thecaxis. The two aromatic rings exhibit a small interplanar angle of 16.03 (9)°.

scholarly journals Crystal structure of 3-[(2-acetylphenoxy)carbonyl]benzoic acid

2014 ◽  
Vol 70 (11) ◽  
pp. o1153-o1153 ◽  
Author(s):  
Mohammad Shoaib ◽  
Ismail Shah ◽  
Syed Wadood Ali Shah ◽  
Muhammad Nawaz Tahir ◽  
Shafi Ullah ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Dihedral Angle ◽  
Title Compound ◽  
Aromatic Rings ◽  
Compound C

In the title compound, C16H12O5, synthesized from isopthaloyl chloride and 2′-hydroxyacetophenone, the dihedral angle between the planes of the aromatic rings is 71.37 (9)°. In the crystal, carboxylic acid inversion dimers generateR22(8) loops. The dimers are linked by C—H...O interactions, generating (101) sheets.

Structural characterization of a modification subunit of a putative type I restriction enzyme fromVibrio vulnificusYJ016

2012 ◽  
Vol 68 (11) ◽  
pp. 1570-1577 ◽  
Author(s):  
Suk-Youl Park ◽  
Hyun-Ju Lee ◽  
Jung-Mi Song ◽  
Jiali Sun ◽  
Hyo-Jeong Hwang ◽  
...  
Keyword(s):  
Vibrio Vulnificus ◽  
Restriction Enzymes ◽  
Type I ◽  
Aromatic Rings ◽  
Recognition Sequence ◽  
Thermus Aquaticus ◽  
Methyl Group ◽  
Cofactor Binding ◽  
Adenine Ring ◽  
Adenine Base

In multifunctional type I restriction enzymes, active methyltransferases (MTases) are constituted of methylation (HsdM) and specificity (HsdS) subunits. In this study, the crystal structure of a putative HsdM subunit fromVibrio vulnificusYJ016 (vvHsdM) was elucidated at a resolution of 1.80 Å. A cofactor-binding site forS-adenosyl-L-methionine (SAM, a methyl-group donor) is formed within the C-terminal domain of an α/β-fold, in which a number of residues are conserved, including the GxGG and (N/D)PP(F/Y) motifs, which are likely to interact with several functional moieties of the SAM methyl-group donor. Comparison with the N6 DNA MTase ofThermus aquaticusand other HsdM structures suggests that two aromatic rings (Phe199 and Phe312) in the motifs that are conserved among the HsdMs may sandwich both sides of the adenine ring of the recognition sequence so that a conserved Asn residue (Asn309) can interact with the N6 atom of the target adenine base (a methyl-group acceptor) and locate the target adenine base close to the transferred SAM methyl group.

On the oxidation of 2-t-Butyl-p-cresol

1978 ◽  
Vol 31 (4) ◽  
pp. 907 ◽  
Author(s):  
FR Hewgill ◽  
GB Howie
Keyword(s):  
Acid Solution ◽  
Ferric Chloride ◽  
Silver Oxide ◽  
Quinone Methide ◽  
Alkaline Solutions ◽  
Aromatic Rings ◽  
Methyl Group

While oxidation of alkaline solutions of 2-t-butyl-p-cresol by ferricyanide or silver oxide gives the ortho-para-coupled Pummerer's ketone (6), ferric chloride in slightly acid solution gives the ortho- coupled biphenyldiol (5). With ddq in methanol the cresol is further oxidized, again through ortho coupling, to the lactone (10), in which one of the aromatic rings has been cleaved, and to the dibenzo-furan (9). Minor products, both monomeric and dimeric, in which the methyl group has been oxidized via the quinone methide, were also identified.

Polysulfonylamine, CLXXIII [1]. Intermolekulare Wechselwirkungen in kristallinen Di(organosulfonyl)aminen. – Teil 2 [2]. Strukturvergleich f ¨ur Di(4-X-benzolsulfonyl)amine mit X = Fluor, Chlor, Brom oder Methyl / Polysulfonylamines, CLXXIII [1]. Intermolecular Interactions in Crystalline Di(organosulfonyl) amines. Part 2 [2]. Comparing the Stuctures of Di(4-X-benzenesulfonyl)amines, where X is Fluorine, Chlorine, Bromine, or Methyl

2005 ◽  
Vol 60 (6) ◽  
pp. 645-658 ◽  
Author(s):  
Dagmar Henschel ◽  
Thomas Hamann ◽  
Oliver Moers ◽  
Peter G. Jones ◽  
Armand Blaschette
Keyword(s):  
Hydrogen Bonds ◽  
The Other ◽  
Halogen Bonds ◽  
Aromatic Rings ◽  
Methyl Group ◽  
X Ray ◽  
Rotation Axes ◽  
Halogen Compounds ◽  
The Face ◽  
Exchange Rule

Low-temperature X-ray structures of the following di(4-X-benzenesulfonyl)amines, HN(SO2-C6H4-X)2, are compared in order to study the effects of the 4-substituents on the molecular packings: X = F (1, monoclinic, C2/c, Z′ = 1), X = Cl (2, monoclinic, C2/c, Z′ = 1/2, N-H bonds lying on twofold rotation axes), X = Me (3, orthorhombic, Pbca, Z′ = 1), X = Br (4A, monoclinic, P21/c, Z′ = 1), X = Br (4B, monoclinic, P21/c, Z′ = 2). As a common feature, the molecules of the halogen compounds, including two polymorphs of 4, are associated into catemers by strong hydrogen bonds of the type N-H···O in 1, 4A and 4B or N-H(···O)2 in 2. These molecular chains are assembled in the crystal structures via different packing modes, which underline the well-known correlation between the atomic number of halogen atoms and their propensity to form halogen bonds. Thus, the structure of 1 is devoid of short C-F···O/N contacts, but close F···F contacts are tolerated, whereas in 2 each catemer is connected to four parallel congeners by long and bifurcated C-Cl(···O)2 bonds, and both polymorphs of 4 display layers in which the molecules are connected by N-H···O bonds in one and by relatively short and approximately linear C-Br···O interactions in the other dimension. Despite the alleged steric equivalence of methyl and chloro substituents (“chloro-methyl exchange rule”), the packing architecture of the methyl compound 3 is not related to any of the preceding structures. In this case, the N-H···O bonding leads to centrosymmetric cyclodimers, which pack in such a way that each methyl group is located between two oxygen atoms and above the face of an aromatic ring in a topology consistent with C-H···O and C-H···C(π) bonding. All the structures are pervaded by weak Car-H···O hydrogen bonds; moreover, 1 displays a short C-H···F hydrogen bond and a C-F···C(π) interaction, and π-stacking of aromatic rings is observed in 1, 3 and 4B

Microcalorimetric adsorption and infrared spectroscopic studies of supported Pd, Ru and Pd–Ru catalysts for the hydrogenation of aromatic rings with carboxyl groups

2021 ◽  
Author(s):  
Shiling Zhao ◽  
Jingxuan Cai ◽  
Qiumei Hou ◽  
Danyang Zhao ◽  
Jianyi Shen
Keyword(s):  
Benzoic Acid ◽  
High Activity ◽  
Chemical Properties ◽  
Spectroscopic Studies ◽  
Carboxyl Groups ◽  
Surface Chemical ◽  
Aromatic Rings ◽  
Ru Catalysts ◽  
Special Surface ◽  
Supported Pd

Pd–Ru/SiO2 showed special surface chemical properties that were totally different from those of Pd/SiO2 and Ru/SiO2 and exhibited high activity and selectivity for the hydrogenation of benzoic acid to cyclohexanecarboxylic acid.

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