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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Cholinergic agonists or cholinomimetics mimic the action of acetylcholine to stimulate the parasympathetic nervous system. They are categorized into direct-acting and indirect-acting agents. The direct-acting cholinergic drugs induce the parasympathetic response by directly binding to the muscarinic or nicotine receptors. In comparison, the indirect-acting cholinergic drugs prevent acetylcholine hydrolysis, indirectly contributing to the extended parasympathetic response.
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Diazonium Group Substitution: –OH and –H01:19

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Cholinergic Antagonists: Chemistry and Structure-Activity Relationship01:29

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Cholinergic antagonists bind to cholinergic receptors and limit the effects of acetylcholine and other cholinergic agonists. Based on the specific cholinergic receptor affinity, these antagonists are classified as muscarinic or nicotinic. Anticholinergics interrupt parasympathetic innervations while sympathetic innervations remain uninterrupted. Muscarinic antagonists are also called 'muscarinic antagonists', 'antimuscarinics', or 'parasympatholytics'. Nicotinic...
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Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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4-Amino-3,5-di-chloro-pyridine.

Thankappan Ramalakshmi Anantheeswary1, Sundaramoorthy Gomathi1, Ramu Shyamaladevi1

  • 1Department of Chemistry, Periyar Maniammai Institute of Science & Technology, Thanjavur, Tamilnadu-613403, India.

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Summary

This study details the crystal structure of C5H4Cl2N2, revealing molecular assembly via hydrogen bonding and pi-stacking interactions. Hirshfeld analysis quantifies these interactions, crucial for understanding crystal packing and material properties.

Keywords:
4-amino-3,5-di­chloro­pyridinecrystal structurehalogen–π inter­action. Hirshfeld surface analysisoffset π–π stacking

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Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Solid-State Chemistry

Background:

  • Understanding intermolecular forces is key to designing materials with specific properties.
  • Crystal structure analysis provides insights into molecular arrangement and interactions.
  • Computational methods aid in quantifying these interactions.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of the title compound (C5H4Cl2N2).
  • To analyze the contribution of various interactions (hydrogen bonding, pi-stacking, halogen-pi) to crystal packing.
  • To quantify the role of Coulombic forces in the overall crystal energy.

Main Methods:

  • Single-crystal X-ray diffraction for structural determination.
  • Hirshfeld surface analysis to quantify intermolecular contacts.
  • Energy framework analysis using computational chemistry (CE-B3LYP/6-31G(d,p)).

Main Results:

  • The compound crystallizes with one molecule in the asymmetric unit.
  • Supramolecular chains are formed via N-H⋯N hydrogen bonding, interconnected by pi-pi stacking and halogen-pi interactions.
  • Hirshfeld analysis highlights significant Cl⋯H/H⋯Cl (40.1%) and H⋯H (15.7%) interactions.
  • Energy framework analysis indicates a substantial contribution of Coulombic interactions to crystal packing.

Conclusions:

  • The crystal structure is stabilized by a combination of hydrogen bonding, pi-stacking, and halogen-pi interactions.
  • Hirshfeld surface analysis provides a quantitative measure of the dominant intermolecular forces.
  • Computational analysis confirms the importance of Coulombic interactions in the crystal lattice energy.