一种有机-六氯斯坦酸杂化化合物的合成:一种桥接三环有机盐酸盐通过在其晶体结构中填充来稳定

IF 4.9 2区 化学 Q2 CHEMISTRY, PHYSICAL Journal of Molecular Structure Pub Date : 2025-07-05 Epub Date: 2025-03-04 DOI:10.1016/j.molstruc.2025.141942
Kevin Salamanca-Perdigón , Diana M. Ardila , Álvaro Campos , Johan D. Lozano , Federico Ramírez , Alirio Palma , Jaime Portilla , Mario A. Macías
{"title":"一种有机-六氯斯坦酸杂化化合物的合成:一种桥接三环有机盐酸盐通过在其晶体结构中填充来稳定","authors":"Kevin Salamanca-Perdigón ,&nbsp;Diana M. Ardila ,&nbsp;Álvaro Campos ,&nbsp;Johan D. Lozano ,&nbsp;Federico Ramírez ,&nbsp;Alirio Palma ,&nbsp;Jaime Portilla ,&nbsp;Mario A. Macías","doi":"10.1016/j.molstruc.2025.141942","DOIUrl":null,"url":null,"abstract":"<div><div>The use of 2-aminopyrazine in preparing organo-hexachlorostannates compounds has not been reported. Literature shows few reports related to the functionalization of this aromatic ring, indicating that the chemistry associated with this compound has not been sufficiently explored. In this work, a new organo-hexachlorostannate (OHcs) compound has been isolated using a simple experimental protocol dissolving SnCl<sub>2</sub><sup>.</sup>2H<sub>2</sub>O in concentrated hydrochloric acid. This compound is described as an isolated octahedra hexachlorostannate [SnCl<sub>6</sub>]<sup>2-</sup> anion conforming the crystal structure with the organic moiety 3,7-diamino-1,2,4a,5,8,8a-hexahydro-8,5-(epiminomethano)pyrido[3,4-<em>b</em>]pyrazin-10-ol which is present in its multi-protonated hydrochloric salt form. X ray diffraction analysis was performed to determine the structure of crystals grown by slow evaporation after the reaction process. Additionally, infrared spectroscopy (IR), high-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), and differential scanning calorimetry (DCS) techniques were used to characterize the product. Considering the lack of reports in the literature, this work concludes that this compound is only stable in the solid state due to packing stabilization. However, a reversible reaction favoring the formation of 2-aminopyrazine hydrochloride takes place in solution. Following the results from these experiments, we propose that this organo-hexachlorostannate hybrid compound is formed through a multi-step synthesis via Stephen reduction and an inverse electron demand Diels-Alder (IEDDA) cycloaddition which opens interesting alternatives to synthesize new polycyclic compounds.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1334 ","pages":"Article 141942"},"PeriodicalIF":4.9000,"publicationDate":"2025-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of an organo-hexachlorostannate hybrid compound: A case of a bridged tricyclic organic hydrochloric salt stabilized by the packing in its crystal structure\",\"authors\":\"Kevin Salamanca-Perdigón ,&nbsp;Diana M. Ardila ,&nbsp;Álvaro Campos ,&nbsp;Johan D. Lozano ,&nbsp;Federico Ramírez ,&nbsp;Alirio Palma ,&nbsp;Jaime Portilla ,&nbsp;Mario A. Macías\",\"doi\":\"10.1016/j.molstruc.2025.141942\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The use of 2-aminopyrazine in preparing organo-hexachlorostannates compounds has not been reported. Literature shows few reports related to the functionalization of this aromatic ring, indicating that the chemistry associated with this compound has not been sufficiently explored. In this work, a new organo-hexachlorostannate (OHcs) compound has been isolated using a simple experimental protocol dissolving SnCl<sub>2</sub><sup>.</sup>2H<sub>2</sub>O in concentrated hydrochloric acid. This compound is described as an isolated octahedra hexachlorostannate [SnCl<sub>6</sub>]<sup>2-</sup> anion conforming the crystal structure with the organic moiety 3,7-diamino-1,2,4a,5,8,8a-hexahydro-8,5-(epiminomethano)pyrido[3,4-<em>b</em>]pyrazin-10-ol which is present in its multi-protonated hydrochloric salt form. X ray diffraction analysis was performed to determine the structure of crystals grown by slow evaporation after the reaction process. Additionally, infrared spectroscopy (IR), high-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), and differential scanning calorimetry (DCS) techniques were used to characterize the product. Considering the lack of reports in the literature, this work concludes that this compound is only stable in the solid state due to packing stabilization. However, a reversible reaction favoring the formation of 2-aminopyrazine hydrochloride takes place in solution. Following the results from these experiments, we propose that this organo-hexachlorostannate hybrid compound is formed through a multi-step synthesis via Stephen reduction and an inverse electron demand Diels-Alder (IEDDA) cycloaddition which opens interesting alternatives to synthesize new polycyclic compounds.</div></div>\",\"PeriodicalId\":16414,\"journal\":{\"name\":\"Journal of Molecular Structure\",\"volume\":\"1334 \",\"pages\":\"Article 141942\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2025-07-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Molecular Structure\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0022286025006283\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/3/4 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Structure","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022286025006283","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/3/4 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0

摘要

使用2-氨基吡嗪制备有机六氯斯坦酸化合物尚未见报道。文献显示很少有关于该芳香环功能化的报道,表明与该化合物相关的化学尚未得到充分的探索。本文采用简单的实验方法,将SnCl2.2H2O溶解于浓盐酸中,分离出一种新的有机六氯斯坦酸(OHcs)化合物。该化合物是一种分离的八面体六氯锡酸盐[SnCl6]2-阴离子,其晶体结构与以多质子化盐酸形式存在的有机部分3,7-二氨基-1,2,4a,5,8,8 - a-六氢-8,5-(亚胺甲醇)吡啶[3,4-b]吡嗪-10-醇一致。通过X射线衍射分析确定反应过程后缓慢蒸发生长的晶体结构。此外,利用红外光谱(IR)、高分辨率质谱(HRMS)、核磁共振(NMR)、热重分析(TGA)和差示扫描量热法(DCS)技术对产品进行了表征。考虑到文献报道的缺乏,这项工作的结论是,由于填料稳定,该化合物仅在固态下稳定。然而,溶液中发生有利于2-氨基吡嗪盐酸盐形成的可逆反应。根据这些实验的结果,我们提出这种有机六氯斯坦酸杂化化合物是通过Stephen还原和逆电子需求Diels-Alder (IEDDA)环加成的多步合成形成的,这为合成新的多环化合物开辟了有趣的选择。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Synthesis of an organo-hexachlorostannate hybrid compound: A case of a bridged tricyclic organic hydrochloric salt stabilized by the packing in its crystal structure
The use of 2-aminopyrazine in preparing organo-hexachlorostannates compounds has not been reported. Literature shows few reports related to the functionalization of this aromatic ring, indicating that the chemistry associated with this compound has not been sufficiently explored. In this work, a new organo-hexachlorostannate (OHcs) compound has been isolated using a simple experimental protocol dissolving SnCl2.2H2O in concentrated hydrochloric acid. This compound is described as an isolated octahedra hexachlorostannate [SnCl6]2- anion conforming the crystal structure with the organic moiety 3,7-diamino-1,2,4a,5,8,8a-hexahydro-8,5-(epiminomethano)pyrido[3,4-b]pyrazin-10-ol which is present in its multi-protonated hydrochloric salt form. X ray diffraction analysis was performed to determine the structure of crystals grown by slow evaporation after the reaction process. Additionally, infrared spectroscopy (IR), high-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), and differential scanning calorimetry (DCS) techniques were used to characterize the product. Considering the lack of reports in the literature, this work concludes that this compound is only stable in the solid state due to packing stabilization. However, a reversible reaction favoring the formation of 2-aminopyrazine hydrochloride takes place in solution. Following the results from these experiments, we propose that this organo-hexachlorostannate hybrid compound is formed through a multi-step synthesis via Stephen reduction and an inverse electron demand Diels-Alder (IEDDA) cycloaddition which opens interesting alternatives to synthesize new polycyclic compounds.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Journal of Molecular Structure
Journal of Molecular Structure 化学-物理化学
CiteScore
7.10
自引率
15.80%
发文量
2384
审稿时长
45 days
期刊介绍: The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.
期刊最新文献
Novel pyrimidine derivatives as potent BUB1B inhibitors for clear cell renal cell carcinoma: From synthesis and characterization to docking insights and therapeutic validation New Os3 carbonyl clusters derived from the reactions of [Os3(CO)10(µ-H)(μ-OH)] and [Os3(CO)10(µ-H)2] with dppbz: Synthesis, structure, reactivity and theoretical calculations Pd-catalyzed synthesis of bithiazole–amide–biaryl conjugates and their antimicrobial, molecular docking, and DFT investigations Structural revision of monobrominated 3-methoxybenzaldehydes: Evidence from X-ray and chemical correlation Characterization of vitamin E succinate inclusion complexes with cyclodextrins: unraveling structure, properties, and mechanism via experimental and molecular modeling study
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1