2-Methyl-5-nitroaniline, structure

ABSTRACT. Second harmonic generation(S.H.G.) in inclusion complexes between dimethyl-cyclodextrin(dimethyl -CD) and nitroaniline derivatives occurs. This is due to the destruction of the centrosyimntric crystal structure in nitroaniline derivatives caused by forming inclusion complexes. S.H.G. intensity of dimethyl /-CD complex with N-methyl-nitroaniline is 5 5 times as large as that of urea. 

Pedras and co-workers (98P1959) isolated a phytoalexin from Wasabi (Wasabia japonica, syn. Eutrema wasabi) and determined its structure to be methyl l-methoxyindole-3-carboxylate (109) (Scheme 38). Compound 109 had already been synthesized by Acheson and co-workers [78JCS(P1)1117] in ten steps from o-nitroaniline. Pedras and co-workers (98P1959) combined our tungstate method and Acheson s work, and synthesized 109 in 9% overall yield but in an impure state. 

Figure 2. The molecular structure of 2-methyl-4-nitroaniline (MNA) as determined by x-ray crystallography (2). Key C, carbon N, nitrogen O, oxygen and H, hydrogen.

For these classes of conjugated molecular and polymer structures, the principal property is that their nonreson-ant, nonlinear optical responses are dominated by ultrafast, virtual excitations of the ir-electron states. This was directly demonstrated by MNA (2-methyl-4-nitroaniline) single crystal measurements of macroscopic second order susceptibilities at do (j 3) and optical frequencies (13-1 ) and combined second harmonic measurements and theo-... 

Hexakis(2,6-di-0-methyl)-a-CyD complexes with a small guest molecule, such as iodine and 1-propanol, crystallize with the cage-type packing structure [185]. Compared with the structure of the corresponding -CyD complex, the guest molecules in the both complexes are shifted to the secondary hydroxyl side from the center of the cavity. 3-Iodopropionic acid [186], m-nitroaniline [187], and acetonitrile [188] are also fully accommodated in the host cage . A 3-0 acetylated host, hexakis(2,6-di-0-methyl-3-0-acetyl)-a-CyD, was crystallized from butylacetate [189]. In spite of the disruption of intramolecular hydrogen bonds, the host molecule is in a round shape because of the inclusion of butylacetate. 

Fig. 7.21. Structures of hexakis 2,3,6-tri-0-methyl)-a-CyD complexes with m-nitroaniline (A) and p-nitrophenol (B).

Phase-matched second harmonic generation in single crystal polymers was first observed in 2-methyl-4-nitroaniline substituted diacetylene polymers. Subsequently, a number of other diacetylene structures... 

OtherNames Aniline,A -methyl-M2,4,6-tetranitro- 2,4,6,A-Tetranitro-A-methylaniline 2,4,6-Tetryl 2,4,6-Trinitro-N-methyl-A-nitroaniline 2,4,6-Trinitrophenyl-A-methylnitramine 2,4,6-Trinitro-phenylmethylnitroamine CE A-Methyl-A,2,4,6-tetranitroaniline A-Methyl-A-picrylnitramine A-Picryl-A-methylnitramine NSC 2166 Nitramine Nitramine (indicator) Picrylmethylnitra-mine Picrylnitromethylamine Tetralit Tetralite Tetril Tetryl CA Index Name Benzenamine, A-methyl-A,2,4,6-tetranitro-CAS Registry Number 479-45-8 Merck Index Number 6573 Chemical Structure... 

Prezhdo, V. V. Bykova, A. S. Prezhdo, O. V. Daszkiewicz, Z. Kyziol, J. B. Zaleski, J. Synthesis, properties, and molecular structure of nitro-substituted IV-methyl-A-nitroanilines. Russ. J. Gen. Ghent. 2006, 76, 64-75. 

Sugihara, O., and Sasaki, K., Phase-matched second-harmonic generation in a 2-methyl-4-nitroaniline single-crystal waveguide combined structure of grating couplers and four-layer waveguide, J. Opt. Soc. Am. B, 9, 104-107 (1992). 

The polarizability and first hyperpolarizability of p-nitroaniline and its methyl-substituted derivatives have been calculated using a non-iterative approximation to the coupled-perturbed Kohn-Sham equation where the first-order derivatives of the field-dependent Kohn-Sham matrix are estimated using the finite field method" . This approximation turns out to be reliable with differences with respect to the fully coupled-perturbed Kohn-Sham values smaller than 1% and 5% for a and p, respectively. The agreement with the MP2 results is also good, which enables to employ this simplified method to deduce structure-property relationships. 

The most common nonlinear optical molecules, with a donor—Ji-system—acceptor structure are, as a rule, neutral in the ground state and become charged in the excited state by electron transfer, in contrast with 4 -[Methyl(diphenyl)phosphonio]biphenyl-4-yl triphenylborate (PBB), which has a high dipole moment in the ground state and a lower one in the excited state. The hyperpolarizability P of PBB is comparable to that of p-nitroaniline and fortunately PBB shows transparency above 400 nm. 

A number of 5- and N-ketosyl derivatives of NANA were prepared by Privalova and Khorlin (1969). The use of p-nitroaniline in a Koenigs-Knorr type reaction with the acetylglycosyl chloride methyl ester of NANA gave (after subsequent deacylation) the 2-deoxy-2-p-nitropheny-lamino A-glycoside of NANA, assigned structure XXXI (Figure 10). 

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