Names | |
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IUPAC name 3,2′:4′,3′′-Terpyridine | |
Other names Nicotellin; 2,4-Dipyridin-3-ylpyridine | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C15H11N3 | |
Molar mass | 233.274 g·mol−1 |
Melting point | 147–148 °C (297–298 °F; 420–421 K) [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Nicotelline is an alkaloid first identified in 1914 as a chemical constituent of tobacco plants (Nicotiana). [2]
The chemical structure of nicotelline wasn't elucidated until 1956, when it was determined that nicotelline is a terpyridine consisting of three linked pyridine rings. [3] This structure was confirmed by laboratory synthesis. [3] [4] Nicotelline has the molecular formula C15H11N3. It is a crystalline solid with a melting point of 147-148 °C. [1] It is soluble in hot water, chloroform, ethanol, and benzene. [1]
Nicotelline has long been known to be a constituent of tobacco smoke. [5] As such, it has recently been proposed as a biomarker or environmental tracer for tobacco smoke. [6]
Adolph Wilhelm Hermann Kolbe was a major contributor to the birth of modern organic chemistry. He was a professor at Marburg and Leipzig. Kolbe was the first to apply the term synthesis in a chemical context, and contributed to the philosophical demise of vitalism through synthesis of the organic substance acetic acid from carbon disulfide, and also contributed to the development of structural theory. This was done via modifications to the idea of "radicals" and accurate prediction of the existence of secondary and tertiary alcohols, and to the emerging array of organic reactions through his Kolbe electrolysis of carboxylate salts, the Kolbe-Schmitt reaction in the preparation of aspirin and the Kolbe nitrile synthesis. After studies with Wöhler and Bunsen, Kolbe was involved with the early internationalization of chemistry through work in London. He was elected to the Royal Swedish Academy of Sciences, and won the Royal Society of London's Davy Medal in the year of his death. Despite these accomplishments and his training important members of the next generation of chemists, Kolbe is best remembered for editing the Journal für Praktische Chemie for more than a decade, in which his vituperative essays on Kekulé's structure of benzene, van't Hoff's theory on the origin of chirality and Baeyer's reforms of nomenclature were personally critical and linguistically violent. Kolbe died of a heart attack in Leipzig at age 66, six years after the death of his wife, Charlotte. He was survived by four children.
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