Plane Of Phenyl Ring Research Articles

Syntheses, Characterization and X-ray Crystal Structure of Trinuclear NiII—NaI—NiII Assembled with Salen-type Schiff Base

The present investigation describes the synthesis and structural study of a metal-zinc ligand [NiL].H2O, which was used to generate a trinuclear complex formulated as {Ni(m-L)Na(m-L)Ni}.(SCN)0.6.(Cl)0.4. The title compound crystallizes in the tetragonal space group I41/acd with the following unit cell parameters: a = 185403(5) Å, c = 51.925(2) Å, V = 17849.0(3) Å3, Z = 16, R1 = 0.074 and wR2 = 0.209. Each organic molecule acts as a hexadentate ligand and bridges Ni(II) and Na(I). For both Ni(II) cations the coordination environment around the metal center can be described as distorted square planar. The Na(I) cation is eight coordinated and the polyhedron around the sodium ions is best described as a distorted square anti-prism. The means planes of the two phenyl rings with a methoxy substituent form a dihedral angle of 3.870(4)°, while the dihedral angle values of these mean planes with the means plane of the central phenyl ring are, respectively, 11.233(4)° and 14.138(3)°. The Zn–Na distance is 3.4285(7) Å. Weak hydrogen bonds involving C—H as donor and Cl, S or O as acceptor are observed.

Ab Initio Determination of Molecular Geometry and Vibrational Frequencies of Benzotrifluoride

Using Gaussian 05 Revision C.02 version of the quantum chemical program ab initio computations has been carried out to compute optimized geometry, harmonic vibrational frequencies along with intensities in IR and Raman spectra and atomic charges at rhf / 6–31+g*, b3lyp / 6–31++g** and b3lyp / 6–311++g** levels. The optimized molecular structure is found to possess Cs point group symmetry with the plane of symmetry passing through the C atom, to which the CF3 group is attached, the centrally opposite C atom and the C atom of the CF3 group and perpendicular to the phenyl ring plane. One of the three F atoms of the CF3 group is found to be on one side of the ring plane and is situated on the plane of the symmetry while the other two F atoms are found to be on the other side of the ring plane placed symmetrically on either side of the symmetry plane. Vibrational assignments for the normal modes have been reviewed. To make vibrational assignments for the normal modes of vibration the Gauss View software was used. The CF3 group has the characteristic frequencies in the 340, 768, 1072, 1152 and 1318 cm-1 which are due to the modes δs (CF3), Vs (CF3 ), Vas(CF3) (a’), Vas(CF3) (a”) and V(C–CF3 ) respectively. The torsional frequency of the CF3 group is found to be 16 cm-1 which would lead to barrier height of ~ 0.5 kJ / mol for the torsional motion of the CF3 group.

Bridged Peptide Analogue of RA-VII, an Antitumor Bicyclic Hexapeptide

AbstractA bridged peptide analogue of RA-VII was designed, in which the α carbons of residues 1 and 4 were linked by a tetramethylene chain to restrict the conformational freedom of the backbone of the 18-membered cyclopeptide. This peptide analogue was synthesized by a ring-closing metathesis reaction of [l-2-allylglycine-1, l-2-allylglycine-4]RA-VII and a subsequent hydrogenation of the resulting olefinic compound. Compared with RA-VII, the analogue showed much weaker cytotoxic activity toward human promyelocytic leukemia HL-60 cells and human colon carcinoma HCT-116 cells, which may be accounted for by the difference in the orientation of the Tyr-6 phenyl ring plane between the analogue and RA-VII.

Structural (at 100 K) and DFT studies of 2'-nitro-flavone.

The geometry of the title mol-ecule [systematic name: 2-(2-nitro-phen-yl)-4H-chromen-4-one], C15H9NO4, is determined by two dihedral angles formed by the mean plane of phenyl ring with the mean planes of chromone moiety and nitro group, being 50.73 (5) and 30.89 (7)°, respectively. The crystal packing is determined by π-π inter-actions and C-H⋯O contacts. The results of DFT calculations at the B3LYP/6-31G* level of theory provided an explanation of the unusually large dihedral angle between the chromone moiety and the phenyl group. The electrostatic potential map on the mol-ecular surface was calculated in order to determine the potential binding sites to receptors.

Lanthanide complexes based on a C3 symmetric tripodal ligand and potential application as fluorescent probe of Fe3+

Based on a novel C3 symmetric tripodal ligand 1,1′,1′′-[(2,4,6-trimethyl-1,3,5-benzenetriyl)tris(methylene)]tris[2(1H)-pyridinone], eight isostructural lanthanide coordination complexes have been constructed. The one-dimensional ladder-like chain structures in these complexes are packed together through the interaction of hydrogen bonding and π-π stacking, leading to the formation of a three-dimensional structure with one-dimensional channels. A systematic study on Ln-O bond lengths in this family of complexes revealed that Ln-O distances exhibited a trend according to the lanthanide contraction. And the torsion angles that define the ligand conformation are different for the pyridone groups on distinct side of the plane of the central phenyl ring. Selected complex from the family shows highly selective and sensitive fluorescence quenching by Fe3+ ion, which is not affected by other common metal ions. The Stern–Volmer curve regarding the fluorescence quenching of Fe3+ toward the complex exhibits perfect linearity for a variety of concentrations, demonstrating the complex to be a good candidate as highly selective, efficient, and quantitative fluorescent probe for Fe3+.

Syn and anti polymorphs of 2,6-dimethoxy benzoic acid and its molecular and ionic cocrystals: Structural analysis and energetic perspective

The conformational polymorphism in 2,6-dimethoxy benzoic acid, in which the acidic hydrogen atom can be either in an anti or a syn conformation with respect to the carbonyl oxygen atom, has been studied. The compound crystallizes in two conformational polymorphic forms, anti and syn. The COOH group lies out of the phenyl ring plane due to steric repulsion with the ortho-methoxy substituents. The acidic O–H bond in the COOH carboxyl group in anti appears to be more polar/ionic compared to the syn form. Both polymorphs were characterized by single-crystal X-ray diffraction and for the anti form a neutron diffraction measurement was carried out. In addition, a new molecular co-crystal (MCC) and a new ionic cocrystal (ICC) form were also obtained and characterized by single crystal X-ray diffraction in which the protonated 2,6-dimethoxy benzoic acid units adopt syn configuration. The crystal packing, hydrogen bonding and intermolecular interactions are discussed in terms of Hirshfeld surface analysis and derived properties such as the contact enrichment ratio and energy frameworks. Cohesive energies based on fully periodic DFT calculations as well as based on the sum of dimeric interaction energies were estimated for both syn and anti forms. They reveal the higher stability of the crystal structure in the anti form while the syn form is more stable in the isolated state. Room temperature Raman spectra were collected on the single crystals of the anti and ionic cocrystal forms and compared with both isolated-molecule and periodic calculations.

Click synthesis and characterization of 1,2,3-triazolium salts

New triazolium compounds: 4-(2-formylphenyl)-3-methyl-1-propyl-1H-1,2,3-triazol-3-ium iodide, 3, 4,4’-(((1E)-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(2,1-phenylene))bis(3-methyl-1-propyl-1H-1,2,3-triazol-3-ium) iodide,4, and, 4-(2-formylphenyl)-3-methyl-1-propyl-1H-1,2,3-triazol-3-ium hexafluorophosphate,5, were synthesized and fully characterized by 1H &13C NMR, EA, IR spectroscopy, MS and single crystal X-ray diffraction analysis for 4 and 5. Compound 3 was obtained by adaptation of the ‘click’ Cu(I) catalyzed [3 + 2] cycloaddition reaction to yield the 1,2,3 triazole that was alkylated with methyl iodide. Schiff base condensation of 3 with a diamine led to the isolation of compound 4 in excellent yield and anion metathesis of 3 with KPF6 yielded 5. The single crystal X-ray diffraction results reveal that both compounds 4 and 5 crystallized in the P-1 space group of the triclinic system. The dihedral angles between the planes of the triazole rings in 4 and 5 and the planes of the respective phenyl rings were found to be 72.8(6)° and 62.8(3)° which is indicative of strong deviation from coplanarity. The solid-state structures of 4 and 5 are further stabilized by weak intramolecular C–H … π and intermolecular C–H … X (X = F, I) non-bonded interactions. Results of Hirshfeld surface contacts analysis and associated two-dimensional fingerprint plots also correlate with the observed intermolecular interactions in the crystals of 4 and 5.

Synthesis, crystal structure, Hirshfeld surface analysis and DNA binding studies of 1-((E)-3-(4-bromophenyl)-1-phenylallylidene)-2-(m-tolyl)hydrazine

1-((E)-3-(4-bromophenyl) -1-phenylallylidene)-2-(m-tolyl)hydrazine (4) was synthesized and characterized for structural elucidation by spectroscopy (FT-IR, 1H NMR, and 13C NMR) and single crystal X-ray diffraction. In the title compound, the benzene rings A, B, C were oriented at dihedral angles {A/B = 82.92 (3)°, A/C = 24.12 (3)°and B/C = 75.90 (3)°}. Crystal structure showed that intermolecular CH⋯O and CH⋯N hydrogen bonds linked the molecules, enclosing R22 (10) and R22 (16) ring motifs. The Hirshfeld surface analysis of the crystal structure indicated that the most important contributions for the crystal packing were from H⋯H (46.0%), H⋯C/C⋯H (17.6%), H⋯Br/Br⋯H (12.4%), H⋯O/O⋯H (8.5%) and C⋯C (6.6%) interactions. Hydrogen bonding and van der Waals contacts were the dominant interactions in the crystal packing. Compound's interaction with DNA was further investigated theoretically by DFT and experimentally by UV–visible spectroscopy and cyclic voltammetry. DFT analysis in terms of geometry optimization and computed parameters revealed reactive nature of 4 and the possibility of planar phenyl rings to intercalate within the DNA base pairs. Spectral and voltammetric analysis and related binding parameters suggested intercalation as a possible mode for 4 – DNA binding which was further verified by viscosity measurements.

Synthesis and crystal structures of 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-benzaldehyde) and 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-isophthalaldehyde).

The title compounds 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-benzaldehyde), C17H16O4, (1), and 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-isophthalaldehyde), C19H16O6, (2), crystallize with one mol-ecule in the asymmetric unit. In mol-ecule (1), a >C(CH3)2 group bridges two nearly planar salicyl-aldehyde groups [r.m.s deviations = 0.010 (1) and 0.025 (2) Å], each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, compound (2) has the same bridging group, but it connects two nearly planar appendants [r.m.s deviations = 0.034 (1) and 0.035 (1) Å], each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Mol-ecule (1) exhibits a bridge angle of 109.5 (2)° with the salicyl-aldehyde planes subtending a dihedral angle of 88.4 (1)°. In contrast, mol-ecule (2) presents a bridge angle of 108.9 (2)° with its appendants subtending a dihedral angle of 79.6 (3)°. Both mol-ecules exhibit two intra-molecular O-H⋯O hydrogen bonds involving the phenolic H atoms and carboxyl O-atom acceptors. In the crystal of (2), O-H⋯O hydrogen bonds between one of the hydroxyl H atoms and a carboxyl O atom from a symmetry-related mol-ecule form a chain along [10]. In addition, (2) exhibits a strong visible luminescence when excited with ultraviolet radiation.

Abnormal Anionic Porphyrin Sensing Effect for HER2 Gene Related DNA Detection via Impedance Difference between MWCNTs and Single-Stranded DNA or Double-Stranded DNA

Human epidermal growth factor receptor 2 (HER2) is a key tumor marker for several common and deadly cancers. It is of great importance to develop efficient detection methods for its over-expression. In this work, an electrochemical impedance spectroscopy (EIS) method adjustable by anionic porphyrin for HER2 gene detection has been proposed, based on the impedance difference between multi-walled carbon nanotubes (MWCNTs) and DNA. The interesting finding herein is that with the addition of anionic porphyrin, i.e., meso-tetra(4-sulfophenyl)-porphyrin (TSPP), the impedance value obtained at a glass carbon electrode (GCE) modified with MWCNTs and a single stranded DNA (ssDNA), the probe DNA that might be assembled tightly onto MWCNTs through π-π stacking interaction, gets a slight decrease; however, the impedance value from a GCE modified with MWCNTs and a double stranded DNA (dsDNA), the hybrid of the probe DNA with a target DNA, which might be assembled loosely onto MWCNTs for the screening effect of phosphate backbones in dsDNA, gets an obvious decrease. The reason may be that on the one hand, being rich in negative sulfonate groups, TSPP will try to push DNA far away from CNTs surface due to its strong electrostatic repulsion towards DNA; on the other hand, rich in planar phenyl or pyrrole rings, TSPP will compete with DNA for the surface of CNTs since it can also be assembled onto CNTs through conjugative interactions. In this way, the “loosely assembled” dsDNA will be repelled by this anionic porphyrin and released off CNTs surface much more than the “tightly assembled” ssDNA, leading to a bigger difference in the impedance value between dsDNA and ssDNA. Thus, through the amplification effect of TSPP on the impedance difference, the perfectly matched target DNA could be easily determined by EIS without any label. Under the optimized experimental conditions, this electrochemical sensor shows an excellent linear response to target DNA in a concentration range of 2.0 × 10−11–2.0 × 10−6 M with a limit of detection (LOD) of 6.34 × 10−11 M (S/N = 3). This abnormally sensitive electrochemical sensing performance resulting from anionic porphyrin for DNA sequences specific to HER2 gene will offer considerable promise for tumor diagnosis and treatment.

Out-of-plane polarization in a layered manganese chloride hybrid

We investigate possible mechanisms to induce electric polarization in layered organic-inorganic hybrids. Specifically, we investigate the structural phase transitions of PEA2MnCl4 (PEA = phenethylamine) using temperature dependent single-crystal X-ray diffraction analysis, including the symmetry analysis of the observed space groups. Our results show that PEA2MnCl4 transforms from a high-temperature centrosymmetric structure with space group I4/mmm to a low-temperature polar Pca21 phase via an intermediate phase with polar space group Aea2. We study the mechanism responsible for the I4/mmm to Aea2 polar phase transition and find that it is different from previously proposed mechanisms in similar systems. The transition is governed by the opening of a small dihedral angle between the phenyl ring planes of two adjacent PEA molecules, which consequently become crystallographically inequivalent in the Aea2 phase. This molecular rotation induces a significant difference in the lengths of the ethylammonium tails of the two molecules, which coordinate the inorganic layer asymmetrically and are consequently involved in different hydrogen bonding patterns. Consequently, the negatively charged chlorine octahedron that coordinates the Mn2+ cation deforms. This deformation moves the Mn2+ off-center along the out-of-plane-axis, contributing to the polar nature of the structure. Notably, the polar axis is out-of-plane with respect to the inorganic sheets. This is in contrast to other layered organic-inorganic hybrids as well as conventional layered perovskites, such as the Aurivillius phases, where in-plane polarization is observed. Our findings add to the understanding of possible mechanisms that can induce ferroelectric behavior in layered organic-inorganic hybrids.

Synthesis and Magnetic Properties of Stable Radical Derivatives Carrying a Phenylacetylene Unit.

A nitronyl nitroxide derivative, 2-phenylethynyl-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl-3-oxide (1), and two verdazyl derivatives carrying a phenylacetylene unit, 1,5-diphenyl-3-phenylethynyl-6-oxo-1,2,4,5-tetrazin-2-yl (2) and 1,5-diisopropyl-3-phenylethynyl-6-oxo-1,2,4,5-tetrazin-2-yl (3), were synthesized and their packing structures were studied by X-ray crystallographic analysis and magnetically characterized in the solid state. While 1 and 3 had an isolated doublet spin state, 2 formed an antiferromagnetically coupled pair (2J/kB = −118 K). Density functional theory (DFT) calculations reveal that the spin density polarized in the phenyl group decreases as the dihedral angle between the phenyl ring and radical plane increases.

Molecular structure and conformational behavior of 1-methyl-1-phenylsilacyclohexane studied by gas electron diffraction, IR spectroscopy and quantum chemical calculations

Conformational properties and molecular structure of 1-methyl-1-phenylsilacyclohexane 1 were studied by quantum chemical (QC) calculations, combined gas electron diffraction/mass spectrometry (GED/MS) and IR spectroscopy. Molecule 1 may exist in four forms that differ by axial or equatorial positions of the substituents and by relative orientation of the two rings. Two of these conformers were found to dominate in the gas phase: 1-Pheq-orth conformer with the phenyl ring plane bisecting the CSiC endocyclic angle, and 1-Phax-twist with the phenyl ring and the CSiC exocyclic angle oriented nearly perpendicularly to each other. From the GED data, the summarized molar fractions of the conformers were found to be Pheq:Phax = 42(15):58(15)% which corresponds to ΔG = Geq–Gax = 0.19(37) kcal/mol. Experimental and calculated IR spectra provides an evidence of existence of both conformers in the liquid phase. The QC calculations yielded the ΔG = G(Pheq–orth)–G(Phax–twist) values of 0.18–0.36 DFT and 0.82 MP2 kcal/mol.

1-Benzyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

In the title molecule, C22H18N2O, the seven-membered ring adopts a boat conformation with the planes of the pendant phenyl rings nearly perpendicular to the plane of the aromatic portion of the benzodiazepine core. Pairwise C—H...π(ring) interactions form inversion dimers which pack in zigzag layers associated through weak C—H...O hydrogen bonds.

Observation of Evidence for the π*-σ* Hyperconjugation in the S1 State of o-, m-, and p-Fluorotoluenes by Double-Resonance Infrared Spectroscopy.

Drastic changes of the methyl internal rotation potential energy functions upon the electronic excitation have been reported for o- and m-fluorotolunes [ Okuyama , K. , Mikami , N. , and Ito , M. J. Phys. Chem. 1985 , 89 , 5617 - 5625 ], and their physical origin has been attributed to the π*-σ* hyperconjugation. To observe direct evidence of the π*-σ* hyperconjugation, double-resonance infrared spectroscopy was carried out in the CH stretching vibrational region in both the S0 and S1 states of jet-cooled o-, m-, and p-fluorotoluenes. In the spectra of both o- and m-fluorotoluenes, some of the methyl CH bands were red-shifted upon the electronic excitation while the residual CH bands stayed in the same frequency region. The normal-mode analysis demonstrated that the shift behavior correlates to the relative conformation between the methyl CH bond and the phenyl ring plane. This conformation-dependent methyl CH bond weakening clearly supports the presence of the π*-σ* hyperconjugation in o- and m-fluorotoluenes. The similar red-shift of the methyl CH bands upon the electronic excitation was seen also in p-fluorotoluene though the magnitude of the shift was much smaller. The mechanism of its internal rotation potential energy behavior, however, can be different from those of the o- and m-isomers.

Supra-molecular architecture in a co-crystal of the N(7)-H tautomeric form of N (6)-benzoyl-adenine with adipic acid (1/0.5).

The asymmetric unit of the title co-crystal, C12H9N5O·0.5C6H10O4, consists of one mol-ecule of N (6)-benzoyl-adenine (BA) and one half-mol-ecule of adipic acid (AA), the other half being generated by inversion symmetry. The dihedral angle between the adenine and phenyl ring planes is 26.71 (7)°. The N (6)-benzoyl-adenine mol-ecule crystallizes in the N(7)-H tautomeric form with three non-protonated N atoms. This tautomeric form is stabilized by intra-molecular N-H⋯O hydrogen bonding between the carbonyl (C=O) group and the N(7)-H hydrogen atom on the Hoogsteen face of the purine ring, forming an S(7) ring motif. The two carboxyl groups of adipic acid inter-act with the Watson-Crick face of the BA mol-ecules through O-H⋯N and N-H⋯O hydrogen bonds, generating an R 2 (2)(8) ring motif. The latter units are linked by N-H⋯N hydrogen bonds, forming layers parallel to (10-5). A weak C-H⋯O hydrogen bond is also present, linking adipic acid mol-ecules in neighbouring layers, enclosing R (2) 2(10) ring motifs and forming a three-dimensional structure. C=O⋯π and C-H⋯π inter-actions are also present in the structure.

(E)-4-Hydroxy-6-methyl-3-[1-(2-phenylhydrazinylidene)ethyl]-2H-pyran-2-one

The title compound, C14H14N2O3, crystallized with three crystallographically independent molecules (A,BandC) in the asymmetric unit. The three molecules each have anEconformation about the C=N bond but differ in the orientation of the phenyl and pyran rings. The dihedral angles between the phenyl and pyran ring planes are 14.30 (1), 28.38 (1) and 25.58 (1)° in moleculesA,BandC, respectively. There is an intramolecular O—H...N hydrogen bond in each molecule with anS(6) ring motif. In the crystal, molecules are linked by N—H...O and C—H...O hydrogen bonds, forming layers parallel to (001), enclosingR22(8) andR33(21) ring motifs. The layers are linkedviaC—H...π interactions, forming bilayers, which are joined by a further C—H...π interaction, forming a three-dimensional structure.

To the limit of gas-phase electron diffraction: Molecular structure of magnesium octa(m-trifluoromethylphenyl)porphyrazine

The gas-phase molecular structure of the magnesium octa(m-trifluoromethylphenyl)porphyrazine (MgC72H32N8F24) has been studied by a synchronous gas-phase electron diffraction and mass spectrometric experiment at T=667(10) K in combination with DFT calculations using B3LYP hybrid method and triple-ζ valence basis sets. The molecule has an equilibrium structure of D4 symmetry. The following values of selected internuclear distances have been determined: rh1, Å: r(Mg–N)=1.979(5), r(N–C)=1.363(3), r(Nmezo–C)=1.334(4), r(Cpyr–CPh)=1.469(3), r(CPh–CF3)=1.510(5), r(C–F)=1.349(3), r(Cα–Cβ)=1.466(3), r(Cβ–Cβ)=1.380(7). A slight (less than 1 to 2 degrees) twisting deformation of the macrocycle from planarity, caused by the presence of the eight bulky PhCF3 substituents, planes of which are turned by 132.6(9) degrees relative to the adjacent pyrrole rings, has been found. The deviation of phenyl ring planes from 90 degrees orientation is caused by stabilizing donor–acceptor interactions between π-natural orbitals of pyrrole and phenyl moieties. Substitution effects and coordination bonding in magnesium porphyrazine complexes, MgPz, MgPzPh8 and MgPz(CF3Ph)8, are discussed. Sensitivity of GED data to long range interatomic distances of large molecules has been shown.

On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole.

The molecular structures of (E)-1-(4-{[1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone, C19H17FN4O, (III), and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole, C17H14ClN5O2, (IV), prepared by reaction of the corresponding β-diketohydrazones with substituted arylhydrazines in acid media, are nonplanar, with the planes of the lateral phenyl rings forming dihedral angles with that of the central pyrazole ring varying from 2.71 (7) to 45.22 (7)°. The crystal structures are supported by C-H...O, C-H...π and π-π weak intermolecular interactions together with some unusual trifurcated C-Cl...Cl-C contacts, which are discussed in detail.

Conformation analysis and computation of energy barrier to rotation about C[sbnd]N bond in para-methylphenyl carbamate and its solvent dependence in comparison with tertiary carbamates and tertiary amides

Barrier to rotation about conjugated CN bond in p-Methyl phenyl carbamate (PMPC) was computed 14–16kcal/mol at three levels of HF, B3LYP and MP2 using 6-311++G∗∗ basis set. The solvent effect and energy barriers about CN bond in PMPC were compared to the case of tertiary carbamates and tertiary amides. Moreover, it is shown that in primary carbamates such as PMPC and tertiary amides isomerisation process passes through TS2 and TS1 respectively, while in tertiary carbamates goes through a combination of both TSs. Furthermore, X-ray analysis which is reported for the first time for primary aryl carbamates demonstrated that the inclusive plane of carbamate functional group is perpendicular to the plane of phenyl ring. The results of computations are completely in agreement with the X-ray data.