Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

Formaldehyde is a simple chemical compound that is used as a building block in obtaining a wide range of products. The versatility of formaldehyde in chemical synthesis becomes evident when it is reacted with <i>N</i>-alkylethylenediamines. Therefore, this paper reports the structure and...

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Bibliographic Details
Main Authors: Raúl Colorado-Peralta, Sonia Araceli Sánchez-Ruiz, Angelina Flores-Parra
Format: Article
Language:English
Published: MDPI AG 2023-06-01
Series:Organics
Subjects:
Online Access:https://www.mdpi.com/2673-401X/4/2/24
Description
Summary:Formaldehyde is a simple chemical compound that is used as a building block in obtaining a wide range of products. The versatility of formaldehyde in chemical synthesis becomes evident when it is reacted with <i>N</i>-alkylethylenediamines. Therefore, this paper reports the structure and reactivity of a series of compounds derived from easily accessible molecules, such as formaldehyde, sodium hydrosulphide, and <i>N</i>-alkylethylenediamines. The 1,3,5-triazines (<b><i>1a</i></b>-<b><i>1d</i></b>) and bis(3-alkyl-imidazolidin-1-yl)methanes (<b><i>2a</i></b>-<b><i>2d</i></b>) were obtained by simple reaction conditions. Additionally, different proportions of sodium hydrosulphide and formaldehyde were used with <i>N</i>-benzylamine to obtain <i>N</i>-benzyltriazinane (<b><i>3</i></b>), <i>N</i>-benzylthiadiazinane (<b><i>4</i></b>) and <i>N</i>-benzyldithiazinane (<b><i>5</i></b>). All these compounds were characterized by analytical, spectroscopic, and spectrometric techniques, such as melting point, solubility, one-dimensional and two-dimensional nuclear magnetic resonance (<sup>13</sup>C, <sup>1</sup>H, <sup>15</sup>N, COSY, HETCOR, NOESY, COLOC), elemental analysis, high- and low-resolution mass spectrometry, among others. The structures of compounds <b>4</b> and <b>5</b> were obtained by single-crystal X-ray diffraction. The results show that small variations in the stoichiometry and the reaction conditions significantly influence the products obtained.
ISSN:2673-401X