Enantiopure Schiff bases of amino acid phenylhydrazides: impact of the hydrazide function on their structures and properties†,New Journal of Chemistry

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Enantiopure Schiff bases of amino acid phenylhydrazides: impact of the hydrazide function on their structures and properties†
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2018-03-15 00:00:00 , DOI: 10.1039/c7nj04597b
Nadia Bouzayani _{1,

2,

3,

4,

5} , Sylvain Marque _{6,

7,

8,

9,

10} , Brahim Djelassi _{5,

11,

12,

13} , Yakdhane Kacem _{1,

2,

3,

4,

5} , Jérôme Marrot _{6,

7,

8,

9,

10} , Béchir Ben Hassine _{1,

2,

3,

4,

5}

Affiliation

A rapid and eco-friendly synthesis of new enantiopure Schiff bases 5a–e was performed from various α-amino acid phenylhydrazides and 2-hydroxynaphthaldehyde using microwave or ultrasound irradiation in yields ranging from 57 to 75%. These imines were characterized using ¹H & ¹³C NMR, FTIR, mass and UV-vis spectroscopies. In addition, the solid state molecular structure of 5b was determined by single crystal X-ray diffraction which shows that this compound adopts the zwitterionic form, crystallizing in the non-centrosymmetric orthorhombic system with the space group P2₁2₁2₁. DFT calculations show that the BMK/6-31G(2df,2pd) method in the gas phase is well adapted to describe the geometry of the solid state. Theoretical results corroborate the ionic character of this species in concordance with spectroscopic results and lead to a new thin description. The Schiff bases 5a–e behave as organic semiconductors with E_og ≈ 2.77 eV. The in vitro antibacterial study showed that these molecules exhibited various levels of antibacterial effect against all of the tested bacterial strains.

中文翻译：

氨基酸苯基酰肼的对映体纯席夫碱：酰肼功能对其结构和性质的影响†

使用微波或超声波辐照，从各种α-氨基酸苯基酰肼和2-羟基萘乙醛快速合成新的对映纯Schiff碱5a-e，产率为57％至75％。这些亚胺使用¹ H和¹³ C NMR，FTIR，质谱和UV-可见分光光度法进行表征。此外，的固态分子结构图5b是由这表明该化合物采用两性离子形式，在非中心对称斜方晶系，空间群结晶单晶X-射线衍射测定P 2 ₁ 2 ₁ 2 ₁。DFT计算表明，气相的BMK / 6-31G（2df，2pd）方法非常适用于描述固态的几何形状。理论结果与光谱结果一致，证实了该物种的离子特性，并导致了新的描述。Schiff碱5a–e表现为有机半导体，E _og≈2.77 eV。的体外抗菌研究表明，这些分子表现出针对所有测试的细菌菌株的抗菌作用的各种水平。

更新日期：2018-03-15

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