The X-ray crystal structures of three N-heterocyclic germylenes (NHGes) have been elucidated including the previously unknown 1,3-bis(2,6-dimethylphenyl)diazagermol-2-ylidene (1). In addition, the X-ray crystal structures of the previously synthesised 1,3-bis(2,4,6-trimethylphenyl)diazagermol-2-ylidene (2) and 1,3-bis(2,6-diisopropylphenyl)diazagermol-2-ylidene (3) are also reported. The discrete molecular structures of compounds 1 to 3 are comparable, with Ge-N bond lengths in the range 1.835-1.875 &#xc5;, while the N-Ge-N bond angles range between 83.6 and 85.2&#xb0;. Compound 2 was compared to the analogous N-heterocyclic carbene species, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes). The major geometrical difference observed, as expected, was the bond angle around the divalent group 14 atom. The N-Ge-N bond angle was 83.6&#xb0; for compound 2 versus the N-C-N bond angle of 101.4&#xb0; for IMes. The Sn equivalent of (1), 1,3-bis(2,6-dimethylphenyl)diazastannol-2-ylidene (4), has also been synthesised and its crystal structure is reported here. In order to test their suitability as ligands, compounds 1 to 3 were reacted with a wide range of transition metal complexes. No NHGes containing metal complexes were observed. In all cases the NHGe either degraded or gave no reaction.

Christopher A. Dodds

Alan R. Kennedy

Mark D. Spicer

N-Heterocyclic Germylenes: Structural Characterisation of Some Heavy Analogues of the Ubiquitous N-Heterocyclic Carbenes

This contribution sets out to compute thermochemical and geometrical parameters of the complete series of chlorinated isomers of thiophene based on the accurate chemistry model of CBS-QB3. Herein, we compute standard entropies, standard enthalpies of formation, standard Gibbs free energies of formation, and heat capacities. Our calculated enthalpy values agree with available limited experimental values. The DFT-based reactivity descriptors were used to elucidate the site selectivity for the chlorination sequence of thiophene. The relative preference for chlorination was found to be in accord with the thermodynamic stability trends inferred based on the H scale. Calculated Fukui indices predict a chlorination sequence to ensue as follows: 2-chloro → 2,5-dichloro → 2,3,5-trichloro → 2,3,4,5-tetrachlorothiophene.

Ibrahim A. M. Saraireh

Mohammednoor Altarawneh

Jibril Alhawarin

Mansour H. Almatarneh

A Thermochemical Parameters and Theoretical Study of the Chlorinated Compounds of Thiophene

We describe, herein, the synthesis, full characterization, and optical properties of four different ligands L1-L4 which associate an azo group, an imidazole unit, and a Schiff base fragment. The UV-visible absorption bands are characteristic of <svg xmlns:xlink="http://www.w3.org/1999/xlink" xmlns="http://www.w3.org/2000/svg" width="29.494pt" style="vertical-align:-0.2063899pt" id="M1" height="6.42827pt" version="1.1" viewBox="-0.0498162 -6.22188 29.494 6.42827"><g transform="matrix(.013,0,0,-0.013,0,0)"><path id="g113-238" d="M574 449L545 460C526 432 516 430 487 430C404 430 311 435 226 435C104 435 56 379 25 341L43 318C81 354 121 372 181 372C161 246 87 53 23 3L30 -12C48 -12 88 -4 113 11C157 75 207 248 232 371L386 367L326 109C321 86 318 66 318 50C318 4 339 -12 366 -12C410 -12 461 21 505 69L492 96C467 79 434 60 418 60C406 60 400 78 411 147C422 217 439 300 457 366C487 366 524 367 536 370C547 385 558 408 574 449Z"/></g><g transform="matrix(.013,0,0,-0.013,11.316,0)"><path id="g117-149" d="M567 230V280H69V230H567Z"/></g><g transform="matrix(.013,0,0,-0.013,17.092,0)"><path id="g117-148" d="M901 255C861 290 790 361 716 442L694 427L796 280H69V230H796L694 83L716 68C790 149 861 220 901 255Z"/></g></svg><svg xmlns:xlink="http://www.w3.org/1999/xlink" xmlns="http://www.w3.org/2000/svg" width="15.499pt" style="vertical-align:-0.2063899pt" height="6.42827pt" version="1.1" viewBox="33.1531838 -6.22188 15.499 6.42827"><g transform="matrix(.013,0,0,-0.013,33.203,0)"><use xlink:href="#g113-238"/></g><g transform="matrix(.013,0,0,-0.013,40.887,0)"><path id="g113-43" d="M471 153C471 170 463 194 452 212C400 220 373 229 322 255C373 281 400 290 452 298C463 316 471 339 471 357C456 366 431 371 410 370C377 329 356 310 308 279C311 336 317 364 336 413C326 432 310 451 294 459C279 451 262 432 252 413C271 364 277 336 280 279C232 310 211 329 178 370C157 371 132 367 117 357C117 340 125 316 136 298C188 290 215 281 266 255C215 229 188 220 136 212C125 194 117 171 117 153C132 144 157 139 178 140C211 181 232 200 280 231C277 174 271 146 252 97C262 78 278 59 294 51C309 59 326 78 336 97C317 146 311 174 308 231C356 200 377 181 410 140C431 139 456 143 471 153Z"/></g></svg> and <svg xmlns:xlink="http://www.w3.org/1999/xlink" xmlns="http://www.w3.org/2000/svg" width="28.336pt" style="vertical-align:-0.2063899pt" id="M2" height="6.42827pt" version="1.1" viewBox="-0.0498162 -6.22188 28.336 6.42827"><g transform="matrix(.013,0,0,-0.013,0,0)"><path id="g113-111" d="M495 86L479 114C446 82 419 66 409 66C401 66 401 72 406 97C420 166 436 231 453 297C489 435 454 448 428 448C406 448 384 439 354 422C305 394 222 327 161 247H159L183 345C200 415 194 448 173 448C143 448 82 410 23 351L38 325C64 349 95 371 105 371C111 371 116 365 109 336L25 -4L31 -12C50 -4 77 3 107 9C119 69 132 122 145 168C197 254 321 381 370 381C387 381 393 374 378 305L329 95C309 17 320 -12 345 -12C372 -12 430 19 495 86Z"/></g><g transform="matrix(.013,0,0,-0.013,10.158,0)"><use xlink:href="#g117-149"/></g><g transform="matrix(.013,0,0,-0.013,15.934,0)"><use xlink:href="#g117-148"/></g></svg><svg xmlns:xlink="http://www.w3.org/1999/xlink" xmlns="http://www.w3.org/2000/svg" width="15.495pt" style="vertical-align:-0.2063899pt" height="6.42827pt" version="1.1" viewBox="31.995183800000003 -6.22188 15.495 6.42827"><g transform="matrix(.013,0,0,-0.013,32.045,0)"><use xlink:href="#g113-238"/></g><g transform="matrix(.013,0,0,-0.013,39.729,0)"><use xlink:href="#g113-43"/></g></svg> transitions with an additional charge transfer between the azobenzene moiety and the imino group. Finally the determination of MIC80 values against pathogenic fungi such as S. apiospermum, A. fumigatus, and C. albicans revealed that these ligands have effective antifungal properties with highest activities (MIC80) on C. albicans for the azole based ligands L1-L3. DPPH radical scavenging of the studied ligands was also tested.

Siham Slassi

Adeline Fix-Tailler

G&#xe9;rald Larcher

Amina Amine

Abdelkrim El-Ghayoury

Imidazole and Azo-Based Schiff Bases Ligands as Highly Active Antifungal and Antioxidant Components

A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-Chloro-3-((2-(piperidin-1-yl)ethyl)amino)naphthalene-1,4-dione 3g and 2,5-dichloro-3-ethoxy-6-((2,4,6-trifluorophenyl)amino)cyclohexa-2,5-diene-1,4-dione 17 were the most potent, with a minimum inhibitory concentration value of 15.6 &#x3bc;g/mL against test-culture M. luteum and S. aureus, respectively. Furthermore, in this work, a catalase activity of benzo- and naphthoquinone derivatives was examined for the first time. The catalase activity of benzo- and naphthoquinone derivatives was determined, showing that compound 3g had significant inhibition activity for catalase enzyme.

Semih Kurban

Nahide Gulsah Deniz

Cigdem Sayil

Mustafa Ozyurek

Kubilay Guclu

Maryna Stasevych

Viktor Zvarych

Olena Komarovska-Porokhnyavet

Volodymyr Novikov

Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted

A facile Selectfluor-mediated oxidative method for direct introduction of SCN and SeCN groups into diversely substituted indoles and carbazoles is described, by employing readily available thiocyanate and selenocyanate salts, and the scope of the method is underscored by providing 24 examples. The feasibility to sequentially introduce SCN followed by SeCN on a carbazole framework and to synthesize the corresponding S-tetrazole and Se-tetrazole derivatives is also demonstrated.

Rodrigo Abonia

Luisa F. Gutierrez

Angela T. Zwarycz

Sebasti&#xe1;n Correa Smits

Kenneth K. Laali

An Efficient Selectfluor-Mediated Oxidative Thio- and Selenocyanation of Diversely Substituted Indoles and Carbazoles

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Heteroatom Chemistry publishes research on compounds containing main-group elements of groups 13 through 17 of the Periodic Table, with a fundamental focus on the reactivity of heteroatoms.

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Heteroatom Chemistry publishes research on compounds containing main-group elements of groups 13 through 17 of the Periodic Table, with a fundamental focus on the reactivity of heteroatoms.

Heteroatom Chemistry