Synthetic, structural, and biological studies of organotin(IV) derivatives of 6-amino-2-(methyleneamino)hexanoic acid

L-lysine monohydrate was treated with formaldehyde to produce 6-amino-2-(methyleneamino)hexanoic acid (LH) whose potassium salt (LK) was further refluxed with R 2 SnCl 2 (R = Me, 1; n-Bu, 2; Ph, 3) or R 3 SnCl (R = Me, 4; n-Bu, 5; Ph, 6) in methanol to yield the organotin(IV) products (1-6). FTIR sp...

Full description

Saved in:
Bibliographic Details
Published in:Journal of coordination chemistry 2024-01, Vol.77 (1-2), p.203-218
Main Authors: Hussain, Shabbir, Kanwal, Fauzia, Tariq, Muhammad, Parveen, Bushra, Rauf, Abdur, Rasool, Lubna, Nawaz, Samia, Shahid, Muhammad, Batoo, Khalid Mujasam, Hussain, Sajjad, Ibrahim, Ahmed Ahmed
Format: Article
Language:English
Subjects:
antibacterial
Chelation
Chemical composition
computational
Dipole moments
E coli
Energy levels
Hexanoic acid
Lysine
Molecular orbitals
NMR
Nuclear magnetic resonance
organotin(IV)
Potassium salts
Schiff base
Shielding
Spectra
spectroscopy
Spectrum analysis
Stability analysis
Thermal stability
Thermogravimetric analysis
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:L-lysine monohydrate was treated with formaldehyde to produce 6-amino-2-(methyleneamino)hexanoic acid (LH) whose potassium salt (LK) was further refluxed with R 2 SnCl 2 (R = Me, 1; n-Bu, 2; Ph, 3) or R 3 SnCl (R = Me, 4; n-Bu, 5; Ph, 6) in methanol to yield the organotin(IV) products (1-6). FTIR spectroscopy displayed chelating coordination of the carboxylate group and a trigonal bipyramidal geometry of tin in the solid-state which was also verified by computational studies. 1 H NMR spectra displayed signals of ligand skeleton and organotin(IV) moieties. Microanalysis (CHN) data agreed well with the molecular composition of products. Thermogravimetric analysis (TGA) showed highest thermal stability of 5. HOMO and LUMO energy levels are −5.44 to −6.04 and −0.10 to +0.1 eV, respectively. The smallest and highest energy (between HOMO and LUMO) were observed in 1 and 6, respectively. The order of dipole moment is 1 > 4>5 > 3>6 > 2. The significant shielding and de-shielding phenomena observed in 13 C NMR spectra of 3 and 6 can be attributed to the existence of delocalized electrons. Antibacterial potential (disc diffusion method) decreased in the order Ciprofloxacin > 1 > 3>6 > 4>2 > 5>LH against Escherichia coli and 1 > 3 = Ciprofloxacin > 4 ≥ 6 > 2>5>LH against Staphylococcus aureus.
ISSN:0095-8972
1029-0389
DOI:10.1080/00958972.2024.2303628