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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
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Crystal Field Theory - Octahedral Complexes02:58

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Crystal Field Theory
To explain the observed behavior of transition metal complexes (such as colors), a model involving electrostatic interactions between the electrons from the ligands and the electrons in the unhybridized d orbitals of the central metal atom has been developed. This electrostatic model is crystal field theory (CFT). It helps to understand, interpret, and predict the colors, magnetic behavior, and some structures of coordination compounds of transition metals.
CFT focuses on...
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Structure of Amines

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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
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Amines: Introduction01:07

Amines: Introduction

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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Zinc(II) salphen complex-based fluorescence optical sensor for biogenic amine detection.

Muhammad Ameerullah Sahudin1, Mohd Sukor Su'ait2, Ling Ling Tan3

  • 1Centre for Advanced Materials and Renewable Resources (CAMARR), Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600, Bangi, Selangor, Malaysia.

Analytical and Bioanalytical Chemistry
|August 9, 2019
PubMed
Summary

Researchers developed a new optical sensor using a zinc(II) salphen complex to detect histamine, a key biomarker for food freshness. This sensor offers high sensitivity and selectivity, crucial for ensuring food safety and quality in the food industry.

Keywords:
Biogenic aminesHistamineOptical sensorZinc(II) salphen

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Area of Science:

  • Analytical Chemistry
  • Materials Science
  • Food Science

Background:

  • Biogenic amines are critical biomarkers for assessing food freshness and quality.
  • Existing methods for biogenic amine detection lack the speed and simplicity required for the food industry.
  • There is a need for novel sensing materials and techniques for rapid biogenic amine analysis.

Purpose of the Study:

  • To develop a new optical sensing material for histamine detection based on zinc(II) salphen complexes.
  • To create a highly sensitive and selective optical sensor for biogenic amines using the developed material.
  • To evaluate the sensor's performance for potential application in the food industry for quality control.

Main Methods:

  • Synthesis and characterization of three zinc(II) salphen complexes with varying electron-withdrawing groups.
  • Investigation of the fluorescence enhancement upon binding of histamine to the zinc(II) complexes.
  • Immobilization of the most effective complex (complex 2) onto silica microparticles to create an optical sensor.
  • Evaluation of the sensor's limit of detection, linear working range, reproducibility, and selectivity.

Main Results:

  • All synthesized zinc(II) salphen complexes showed high affinity for histamine, with significant fluorescence enhancement upon binding.
  • Complex 2 exhibited superior optical properties and was selected for sensor development.
  • The developed optical sensor demonstrated a very low limit of detection for histamine (4.4 × 10-12 M) and a wide linear working range.
  • The sensor showed excellent reproducibility (RSD 5.5 %) and high selectivity for histamine and cadaverine over other tested amines.

Conclusions:

  • The developed zinc(II) salphen complex-based optical sensor is a promising tool for sensitive and selective detection of histamine.
  • The sensor's performance indicates its potential for practical application in the food industry for monitoring food freshness and ensuring safety.
  • This work contributes to the development of advanced analytical methods for food quality assessment.