Naslov
Computational study of triguanide cyclization

Autori
Štrukil, Vjekoslav ; Glasovac, Zoran ; Eckert-Maksić, Mirjana

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
11th European Symposium on Organic Reactivity : ESOR : Book of Abstracts / Concalves, Pedro M. L. ; Lurdes Cristiano, Maria S. - Faro : Digitalinvest, Lda, 2007, 207-207

ISBN
978-972-9341-62-5

Skup
European Symposium on Organic Reactivity (11 ; 2007)

Mjesto i datum
Faro, Portugal, 01.07.2007. - 06.07.2007

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
triguanide cyclization; computational study

Sažetak
Recently, we prepared series of novel pentasubstituted triguanide derivatives1 starting from appropriately monosubstituted guanidines and N, N'-diisopropylcarbodiimide. In some cases, however, this reaction led to formation of cyclic products which were found to be 1, 2, 4, 6-tetrasubstituted derivatives of 1, 3, 5-triazine. For instance, in an attempt to prepare triguanide 3 starting from N, N-dimethylguanidine (1) and N, N'-diisopropylcarbodiimide (2), the only isolated product was 1, 3, 5-triazine derivative 4, as shown in Scheme 1. The product 4 was spectroscopically characterized and its structure confirmed by X-ray diffraction of the perchlorate salt.2 In this work, results of computational study on cyclization of hexamethyltriguanide (CH3- instead of (CH3)2CH- groups in structure 3) to the corresponding triazine will be presented. Geometry optimizations and vibrational analyses were carried at DFT level of theory using B3LYP/6-31G(d) approach. In addition, single point calculations using B3LYP/6-311+G(d, p) method were carried out. The results indicate that the cyclization proceeds via two-step mechanism with the first step being formation of intermediate heterocyclic structure followed by elimination of methylamine, which results in formation of triazine 4.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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