Browse
Submit Data
Databases
API
Help

Dataset Information

22 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A chiral photochromic Schiff base: (R)-4-meth-oxy-2-[(1-phenyl-ethyl)imino-meth-yl]phenol.

ABSTRACT: The title chiral photochromic Schiff base compound, C(16)H(17)NO(2), was synthesized from (R)-1-phenyl-ethyl-amine and 5-methoxy-salicylaldehyde. The mol-ecule of the title compound exists in the phenol-imine tautomeric form. The dihedral angle between the two aromatic rings is 62.61?(11)°. An intra-molecular O-H?N hydrogen bond with an O?N distance of 2.589?(2)?Å is observed. The crystal packing is stabilized by C-H?? inter-actions involving the aromatic ring.

SUBMITTER: Miura Y

PROVIDER: S-EPMC2970391 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A chiral photochromic Schiff base: (R)-4-meth-oxy-2-[(1-phenyl-ethyl)imino-meth-yl]phenol.

Miura Yukie Y Aritake Yoshikazu Y Akitsu Takashiro T

Acta crystallographica. Section E, Structure reports online 20090909 Pt 10

The title chiral photochromic Schiff base compound, C(16)H(17)NO(2), was synthesized from (R)-1-phenyl-ethyl-amine and 5-methoxy-salicylaldehyde. The mol-ecule of the title compound exists in the phenol-imine tautomeric form. The dihedral angle between the two aromatic rings is 62.61 (11)°. An intra-molecular O-H⋯N hydrogen bond with an O⋯N distance of 2.589 (2) Å is observed. The crystal packing is stabilized by C-H⋯π inter-actions involving the aromatic ring. ...[more]

PMID: 21577845

Similar Datasets

Crystal structure of 2-{(R)-[1-(4-bromo-phen-yl)eth-yl]imino-meth-yl}-4-(phenyl-diazen-yl)phenol, a chiral photochromic Schiff base.

Project description:The title chiral photochromic Schiff base compound, C21H18BrN3O, was synthesized from (R)-(+)-1-(4-bromo-phen-yl)ethyl-amine and the salicyl-aldehyde of an azo-benzene derivative. The mol-ecule corresponds to the phenol-imine tautomer, the C=N and N-C bond distances being 1.285?(3) and 1.470?(3)?Å, respectively. The diazenyl group adopts a trans form, with an N=N distance of 1.256?(3)?Å. The hy-droxy group is involved in intra-molecular O-H?N hydrogen bonding. In the crystal, C-H?? inter-actions consolidate the crystal packing of one-dimensional chains, which exhibits short inter-molecular Br?C contacts of 3.400?(3)?Å.

| S-EPMC4645026 | biostudies-literature

4-Meth-oxy-2-[(E)-(phenyl-imino)meth-yl]phenol.

Project description:In the mol-ecule of the title compound, C(14)H(13)NO(2), the two aromatic rings are oriented at a dihedral angle of 0.78?(20)°; with the exception of two methyl H atoms the mol-ecule is essentially planar. The intra-molecular O-H?N hydrogen bond results in the formation of a non-planar, six-membered ring, which adopts a flattened-boat conformation. In the crystal structure, inter-molecular C-H?O hydrogen bonds link the mol-ecules to form parallel networks. There is a C-H?? contact between the methyl group and the benzene ring. A ?-? contact between the benzene and phenyl rings [centroid-centroid distance = 4.681?(5)?Å] is also observed.

| S-EPMC2960573 | biostudies-literature

6-Meth-oxy-2-[(E)-phenyl-imino-meth-yl]phenol.

Project description:The title compound, C(14)H(13)NO(2), was obtained by the condensation reaction of o-vanillin and aniline in ethanol. The mol-ecule adopts the phenol-imine tautomeric form and an E conformation with respect to the azomethine C=N bond. The dihedral angle between the aromatic rings is 30.57?(10)°. In the crystal, mol-ecules are linked by inter-molecular C-H?O hydrogen bonds into zigzag chains parallel to the b axis.

| S-EPMC3099786 | biostudies-literature

4-Phenyl-diazenyl-2-[(R)-(1-phenyl-ethyl)imino-meth-yl]phenol.

Project description:The title chiral photochromic Schiff base compound, C(21)H(19)N(3)O, was synthesized from (R)-1-phenyl-ethyl-amine and the salicylaldehyde of an azobenzene derivative. The mol-ecule corresponds to the phenol-imine tautomer, the C=N and N-C bond distances being 1.279 (3) and 1.477 (3) Å, respectively. An intra-molecular O-H⋯N hydrogen bond occurs. The diazenyl group adopts a trans form with an N=N distance of 1.243 (3) Å.

| S-EPMC2983984 | biostudies-literature

(E)-4-Methyl-2-[(R)-1-phenyl-ethyl-imino-meth-yl]phenol.

Project description:In the title Schiff base, C(16)H(17)NO, the dihedral angle between the two aromatic rings is 63.59?(2)°. A strong intra-molecular O-H?N hydrogen bond is observed between the hydroxyl group and the imine N atom.

| S-EPMC2961494 | biostudies-literature

2-Bromo-4-chloro-6-[(1-phenyl-ethyl)-imino-meth-yl]phenol.

Project description:The title compound, C(15)H(13)BrClNO, is a Schiff base derived from the condensation of equimolar quanti-ties of 3-bromo-5-chloro-salicylaldehyde and 1-phenyl-ethanamine. The structure displays a trans configuration with respect to the imine C=N double bond. The N atom is also involved in an intra-molecular O-H-N hydrogen bond, which stabilizes the configuration of the compound.

| S-EPMC2959591 | biostudies-literature

Synthesis, crystal structure and computational studies of a new Schiff base compound: (E)-4-bromo-2-eth-oxy-6-{[(2-meth-oxy-phen-yl)imino]meth-yl}phenol.

Project description:The title compound, C16H16BrNO3, which shows enol-imine tautomerism, crystallizes in the monoclinic P21/c space group. All non-H atoms of the mol-ecule are nearly coplanar, with a maximum deviation of 0.274?(3)?Å. In the crystal, mol-ecules are held together by weak C-H?O, ?-? and C-H?? inter-actions. The E/Z isomerism and enol/keto tautomerism energy barriers of the compound have been calculated by relaxed potential energy surface scan calculations with DFT methods. To observe the changes in the aromatic ring, HOMA aromaticity indexes were calculated during the scan process. Total energy and HOMA change curves were obtained to visualize results of the scan calculations.

| S-EPMC5947794 | biostudies-literature

3-Meth-oxy-2-[(E)-(4-meth-oxy-phen-yl)imino-meth-yl]phenol.

Project description:The title compound, C(15)H(15)NO(3), adopts the enol-imine tautomeric form. The two rings are twisted with respect to each other, making a dihedral angle of 44.08?(5)°. The 3-methoxy-2-[(E)-(4-methoxyphenyl)-iminomethyl]phenol unit is almost planar, the largest deviation from the mean plane being 0.047?(2)?Å. Such a planar conformation might be related to the occurrence of an intra-molecular O-H?N hydrogen bond. In the crystal, inter-molecular C-H?O hydrogen bonds link the mol-ecules into sheets parallel to (010). These sheets are inter-connected by weak C-H?? inter-actions.

| S-EPMC3051687 | biostudies-literature

2-[(4-Meth-oxy-benz-yl)imino-meth-yl]phenol.

Project description:In the title Schiff base compound, C(15)H(15)NO(2), prepared from 4-meth-oxy-benzyl-amine and salicyl-aldehyde, an intra-molecular O-H?N hydrogen bonds influences the mol-ecular conformation; the two aromatic rings form a dihedral angle of 73.5?(1)°. In the crystal, weak inter-molecular C-H?O inter-actions link the mol-ecules into chains propagating in [010].

| S-EPMC3011435 | biostudies-literature

4-Bromo-2-[(phenyl-imino)-meth-yl]phenol.

Project description:The title compound, C13H10BrNO, is essentially planar (r.m.s. deviation = 0.026?Å) and the dihedral angle between the planes of the two aryl rings is 1.5?(3)°. An intra-molecular O-H?N hydrogen bond generates an S(6) ring.

| S-EPMC4158544 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data