sana buy eh ft akan ar eta anaremte sk | Resa | Christy Wa Beryllole is the first alkaline earth metal antiaromatic molecule dD 2 KATRINA KRAMER | JANUARY 2021 Antiaromatic beryllole monoadduct : Dip". 4 ring current urce: © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ne earth metal and Heterocyclic berllle (left is believed to be the first antiaromatic system that contains is shown right 1c. An electron delocaliation visualisation of the ‘The heterocyclic beryllole isthe frst antiaromatic molecule containing an alkaline earth metal in its system." puncte waldconipaabeseaine tra skal otha anlrrtesnlcbO 222i tesana Baye it aka eta enamine meu Resor | Chany Wels While metals of the p, d and f block of the periodic table have all been shown to engage in r systems, there has never before been any ‘aromatic or antiaromatic compounds containing s-block elements. Alkaline earth metals had been considered simply too inflexible in terms oftheir oxidation states to allow them to participate in 1 bonding. However, a few promising candidates for the first s-block 1 system emerged within the last decade, In 2014, chemists described a magnesiacyclopentadiene, which they calculated to be antiaromatic.2 But the compound's structure ‘couldn't be confirmed, so its antiaromaticity remained theoretical. Only last year, two compounds ~ one containing magnesium, the ‘other berylum — were described that each contained six rr electrons.3 While that could potentially make them aromatic, their _aromaticty was never investigated. Aberyllacyclopentadiene has now become the first confirmed antiaromatic s-block compound, The five-membered ring comprising four carbon atoms and one beryllium shows all the hallmarks of antiaromaticity: itis cyclic, planar and has four r electrons ~ making it ~antiaromatic according to Huckel's rule, Made by a German and indian collaboration by combining a beryllium dichloride complex with dilthium tetraphenylbutadiene, t confirmed beryllle's planarity by x-ray diffraction. Further evidence of the molecule's aromaticty came from the beryllium atoms, e team nuclear magnetic resonance shift, as well as from computational orbital and magnetic shielding analysis. When combined with Ithium sand in diethyl etner, berylole undergoes a two-clectron reduction to a dark red adduct. Unlike in berylole, the carbon-carbon bonds in this adduct are almost equal length — in line with its formally aromatic nature. However, the adduct has two ‘r coordinated lithium dietherate molecules siting on either side of the heterocycle, which prevent it from being considered a classic aromatic species. References 11DK Roy etal Angew. Chem, Int. Ed, 2020, DOI: 10.1002/anie.202014857 2JWel etal, Angew. Chem, Int. Ed, 2014, $3, 5634 (DOI: 10.1002/anie.201310116) 3LA Freeman et al, Inorg, Chem, 2019, 58, 10554 (DOI: 10.1021/acsinorgchem.9b01058) puncte waldconipaabeseaine tra skal otha anlrrtesnlcbO 222i aa