Bulletin of the Chemical Society of Japan published new progress about 1821-27-8. 1821-27-8 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Amine,Benzene, name is Bis(4-nitrophenyl)amine, and the molecular formula is C12H9N3O4, Name: Bis(4-nitrophenyl)amine.
Mori, Nobuo published the artcileIntramolecular hydrogen bonds. V. Aliphatic hydroxy carboxylates, Name: Bis(4-nitrophenyl)amine, the publication is Bulletin of the Chemical Society of Japan (1965), 38(12), 2149-55, database is CAplus.
cf. CA 63, 17169d. The ir spectra of a number of hydroxy carboxylates in CCl4 were measured and the bands were explained on the basis of the possible rotational isomers around the C¦Á-O axis, as shown in I, II, IIIa, and IIIb and their mirror images. The aliphatic esters studied are of the type R1R2C(OH)(CH2)n-1CO2R (IV) (n, R1, R2, and R given): 1, H, H, Et (IVa); 1, Me, H, Me (IVb) (b46 68¡ã); 1, Me, H, Et (IVc); 1, Me, H, iso-Pr (IVd) (b40 74¡ã); 1, Me, Me, Et (IVe); 2, H, H, Me (IVf) (b15 74¡ã); 2, H, H, Et (IVg); 2, Me, H, Me (IVh) (b13 67¡ã); 2, Me, H, Et (IVi); 2, Me, Me, Me (IVj) (b15 67¡ã); 3, Me, H, Et (IVk) (b2 85-7¡ã); 5, H, H, Et (IVl) (b20 138¡ã); 6, H, H, Et (b15 145¡ã); 8, H, H, Et (b2 131-2¡ã); 9, H, H, Et; 10, H, H, Et. The following cyclic esters (V) were studied (R and position of OH given): Me, 1 (Va) (b10 87¡ã, n25D 1.4585); Me, cis-2 (b14 103¡ã, n25D 1.4637); Et, cis-2; Me, trans-2 (b14 112.5¡ã, n25D 1.4634); Et, trans-2; Me, cis-3 (Vb) (b5 113-15¡ã, n25D 1.4658); Me, trans-3 (b6 111-12¡ã n25D 1.4657); Me, cis-4 (Vc) (b12 128¡ã, n25D 1.4684); Me, trans-4 (b12 125¡ã, n25D 1.4669). The ¦Á-OH esters IVa-e and Va showed a strong band due to H bonding with carbonyl oxygen (form I) and a weak one due to H bond with ether oxygen (form II). The frequency of the latter band decreased with increasing number of Me groups attached to the ¦Á-carbon atom. The ratio of the absorbance of the weak band to that of the strong band (Dw/Ds) was substantially constant in ¦Á-esters, but decreased as the alc. alkyl portion of the ester group increased in bulk or in the number of C atoms. The relatively high ratio for Va was explained in terms of possible steric repulsion between the axial H on C-2 and C-6 and the alkoxy group. Of the ¦Â-OH esters studied, IVf and IVg showed bands corresponding to forms I, IIIa and IIIb, while IVh-j showed bands corresponding to forms I, II and a mixture of IIIa and IIIb. The Me group on the ¦Â-carbon atom sterically serve to make the OH and the ester group closer together; the non-bonded forms IIIa and IIIb decrease in proportion, and the form II comes into existence. IVk and IV1 showed 3 bands corresponding to forms I, IIIa, and a mixture of IIIa and IIIb. Higher ¦Ø-hydroxy esters formed no H-bonding. The absence of H-bonding in Vc was due to the instabilization resulting from assuming the boat or twist conformation. The orientation of the ester group in its 1,3-diaxial chair conformation is unfavorable for H-bonding in Vb. Comparison of the H-bonding frequencies of the hydroxy esters with ¦Á,¦Ø-alkanediols and ¦Ø-methoxy alkanols of the series RO(CH2)nOH, where R = Me or H, indicated, the frequency corresponding to form I in esters was much lower, but for form II, it was higher than those of the other series, when the number of members in a ring to be formed through H bonding was equal to 5. When the ring consists of six members or more, the frequencies for forms I and II of the esters were higher than those of both the alkanol series.
Bulletin of the Chemical Society of Japan published new progress about 1821-27-8. 1821-27-8 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Amine,Benzene, name is Bis(4-nitrophenyl)amine, and the molecular formula is C12H9N3O4, Name: Bis(4-nitrophenyl)amine.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia