Keywords
coordination mode
crystal packing
hydrogen bonding.
hydroperoxo ligand
inorganic hydroperoxide
organoelement hydroperoxide
Abstract
Hydroperoxo complexes, that is coordination compounds with directly bound hydroperoxo ligands OOH−, are encountered and applied in various fields such as catalytic oxygenations and functional material precursors. This focus article spotlights a hydroperoxo ligand as a key moiety providing the reactivity of these complexes and stabilization of their crystal structures through hydrogen bonding. The diversity of hydroperoxo coordination types and hydrogen-bonded motifs is demonstrated for the crystalline organoelement and inorganic hydroperoxides presented in the structural databases.
References
.
Chernyshov I.Y., Vener M.V., Prikhodchenko P.V., Medvedev A.G., Lev O., Churakov A.V.
Crystal Growth and Design,
2016
.
Medvedev A.G., Churakov A.V., Prikhodchenko P.V., Lev O., Vener M.V.
Molecules,
2020
.
Medvedev A.G., Sharipov M.Y., Grishanov D.A., Eshtukov A.V., Churakov A.V., Buldashov I.A., Egorov P.A., Lev O., Prikhodchenko P.V.
Mendeleev Communications,
2022
.
Medvedev A.G., Mikhaylov A.A., Shames A.I., Ilyukhin A.B., Churakov A.V., Grishanov D.A., Mel’nik E.A., Tripol’skaya T.A., Lev O., Prikhodchenko P.V.
Inorganic Chemistry,
2020
.
Mikhaylov A.A., Medvedev A.G., Churakov A.V., Grishanov D.A., Prikhodchenko P.V., Lev O.
Chemistry - A European Journal,
2016
.
Medvedev A.G., Mikhaylov A.A., Churakov A.V., Vener M.V., Tripol’skaya T.A., Cohen S., Lev O., Prikhodchenko P.V.
Inorganic Chemistry,
2015
.
Churakov A.V., Prikhodchenko P.V., Lev O., Medvedev A.G., Tripol’skaya T.A., Vener M.V.
Journal of Chemical Physics,
2010
.
Wolanov Y., Lev O., Churakov A.V., Medvedev A.G., Novotortsev V.M., Prikhodchenko P.V.
Tetrahedron,
2010
.
Churakov A.V., Sladkevich S., Lev O., Tripol’skaya T.A., Prikhodchenko P.V.
Inorganic Chemistry,
2010
.
Mikhaylov A.A., Medvedev A.G., Tripol'skaya T.A., Popov V.S., Mokrushin A.S., Krut'ko D.P., Prikhodchenko P.V., Lev O.
Dalton Transactions,
2017
.
Lakshmi V., Mikhaylov A.A., Medvedev A.G., Zhang C., Ramireddy T., Rahman M.M., Cizek P., Golberg D., Chen Y., Lev O., Prikhodchenko P.V., Glushenkov A.M.
Journal of Materials Chemistry A,
2020
.
Mikhaylov A.A., Medvedev A.G., Grishanov D.A., Edison E., Srinivasan M., Sladkevich S., Gun J., Prikhodchenko P.V., Lev O.
ACS Sustainable Chemistry and Engineering,
2020
.
Shames A.I., Lev O., Mikhaylov A.A., Medvedev A.G., Gun J., Prikhodchenko P.V.
Journal of Physical Chemistry C,
2019
.
Medvedev A.G., Mikhaylov A.A., Chernyshov I.Y., Vener M.V., Lev O., Prikhodchenko P.V.
International Journal of Quantum Chemistry,
2019
.
Yasoda K.Y., Mikhaylov A.A., Medvedev A.G., Kumar M.S., Lev O., Prikhodchenko P.V., Batabyal S.K.
Journal of Energy Storage,
2019
.
Mikhaylov A.A., Medvedev A.G., Grishanov D.A., Sladkevich S., Gun J., Prikhodchenko P.V., Xu Z.J., Nagasubramanian A., Srinivasan M., Lev O.
Langmuir,
2018
.
Grishanov D.A., Mikhaylov A.A., Medvedev A.G., Gun J., Nagasubramanian A., Madhavi S., Lev O., Prikhodchenko P.V.
Journal of Colloid and Interface Science,
2018
.
Grishanov D.A., Mikhaylov A.A., Medvedev A.G., Gun J., Prikhodchenko P.V., Xu Z.J., Nagasubramanian A., Srinivasan M., Lev O.
Energy Technology,
2017
.
Medvedev A.G., Mikhaylov A.A., Grishanov D.A., Yu D.Y., Gun J., Sladkevich S., Lev O., Prikhodchenko P.V.
ACS applied materials & interfaces,
2017
.
Lakshmi V., Chen Y., Mikhaylov A.A., Medvedev A.G., Sultana I., Rahman M.M., Lev O., Prikhodchenko P.V., Glushenkov A.M.
Chemical Communications,
2017
.
Yu D.Y., Batabyal S.K., Gun J., Sladkevich S., Mikhaylov A.A., Medvedev A.G., Novotortsev V.M., Lev O., Prikhodchenko P.V.
Main Group Metal Chemistry,
2015
.
Prikhodchenko P.V., Medvedev A.G., Mikhaylov A.A., Tripol'skaya T.A., Cumbal L., Shelkov R., Wolanov Y., Gun J.
Materials Letters,
2014
.
Yu D.Y., Prikhodchenko P.V., Mason C.W., Batabyal S.K., Gun J., Sladkevich S., Medvedev A.G., Lev O.
Nature Communications,
2013
.
Prikhodchenko P.V., Gun J., Sladkevich S., Mikhaylov A.A., Lev O., Tay Y.Y., Batabyal S.K., Yu D.Y.
Chemistry of Materials,
2012
.
Sladkevich S., Gun J., Prikhodchenko P.V., Gutkin V., Mikhaylov A.A., Medvedev A.G., Tripol’skaya T.A., Lev O.
Carbon,
2012
.
Sladkevich S., Mikhaylov A.A., Prikhodchenko P.V., Tripol’skaya T.A., Lev O.
Inorganic Chemistry,
2010
.
Sladkevich S., Gutkin V., Lev O., Legurova E.A., Khabibulin D.F., Fedotov M.A., Uvarov V., Tripol’skaya T.A., Prikhodchenko P.V.
Journal of Sol-Gel Science and Technology,
2008
.
Savariault J.M., Lehmann M.S.
Journal of the American Chemical Society,
1980
.
Szentivanyi H., Stomberg R., Hämäläinen R., Kohl F.X., Seip R.
Acta Chemica Scandinavica,
1984
.
Šimuneková M., Šimunek J., Chrappová J., Schwendt P., Žák Z., Pavelčík F.
Inorganic Chemistry Communication,
2012
.
Shin S.S., Yeom E.J., Yang W.S., Hur S., Kim M.G., Im J., Seo J., Noh J.H., Seok S.I.
Science,
2017
.
Damatov D., Mayer J.M.
Chemical Communications,
2016
.
Skobelev I.Y., Evtushok V.Y., Kholdeeva O.A., Maksimchuk N.V., Maksimovskaya R.I., Ricart J.M., Poblet J.M., Carbó J.J.
ACS Catalysis,
2017
.
Maksimchuk N.V., Maksimov G.M., Evtushok V.Y., Ivanchikova I.D., Chesalov Y.A., Maksimovskaya R.I., Kholdeeva O.A., Solé-Daura A., Poblet J.M., Carbó J.J.
ACS Catalysis,
2018
.
Insertion of Dioxygen into a Platinum−Hydride Bond to Form a Novel Dialkylhydroperoxo Pt(IV) Complex
Wick D.D., Goldberg K.I.
Journal of the American Chemical Society,
1999
.
Denney M.C., Smythe N.A., Cetto K.L., Kemp R.A., Goldberg K.I.
Journal of the American Chemical Society,
2006
.
Ahijado M., Braun T., Noveski D., Kocher N., Neumann B., Stalke D., Stammler H.
Angewandte Chemie - International Edition,
2005
.
Wickramasinghe L.A., Sharp P.R.
Inorganic Chemistry,
2014
.
Piquemal J., Briot E., Brégeault J.
Dalton Transactions,
2013
.
Kuznetsov M.L., Kozlov Y.N., Mandelli D., Pombeiro A.J., Shul’pin G.B.
Inorganic Chemistry,
2011
.
Solomon E.I., Chen P., Metz M., Lee S., Palmer A.E.
Angewandte Chemie - International Edition,
2001
.
Le Carpentier J.-., Mitschler A., Weiss R.
Acta Crystallographica Section B,
1972
.
Van Asselt A., Santarsiero B.D., Bercaw J.E.
Journal of the American Chemical Society,
1986
.
Punniyamurthy T., Velusamy S., Iqbal J.
Chemical Reviews,
2005
.
Rehder D.
Inorganic Chemistry Communication,
2003
.
Neibergall M.B., Stubna A., Mekmouche Y., Münck E., Lipscomb J.D.
Biochemistry,
2007
.
DiPasquale A.G., Kaminsky W., Mayer J.M.
Journal of the American Chemical Society,
2002
.
DiPasquale A.G., Hrovat D.A., Mayer J.M.
Organometallics,
2006
.
Zagorac D., Müller H., Ruehl S., Zagorac J., Rehme S.
Journal of Applied Crystallography,
2019
.
Fukuzumi S., Cho K., Lee Y., Hong S., Nam W.
Chemical Society Reviews,
2020
.
Sankaralingam M., Lee Y., Nam W., Fukuzumi S.
Coordination Chemistry Reviews,
2018
.
Wang C., Chang H., Lai Y., Fang H., Li C., Hsu H., Li Z., Lin T., Kuo T., Neese F., Ye S., Chiang Y., Tsai M., Liaw W., Lee W., et. al.
Journal of the American Chemical Society,
2016
.
Yamaguchi S., Nagatomo S., Kitagawa T., Funahashi Y., Ozawa T., Jitsukawa K., Masuda H.
Inorganic Chemistry,
2003
.
Yamaguchi S., Wada A., Nagatomo S., Kitagawa T., Jitsukawa K., Masuda H.
Chemistry Letters,
2004
.
Itoh K., Hayashi H., Furutachi H., Matsumoto T., Nagatomo S., Tosha T., Terada S., Fujinami S., Suzuki M., Kitagawa T.
Journal of the American Chemical Society,
2005
.
Kindermann N., Dechert S., Demeshko S., Meyer F.
Journal of the American Chemical Society,
2015
.
Ray K., Pfaff F.F., Wang B., Nam W.
Journal of the American Chemical Society,
2014
.
Medvedev A.G., Grishanov D.A., Mikhaylov A.A., Churakov A.V., Tripol’skaya T.A., Ottenbacher R.V., Bryliakov K.P., Shames A.I., Lev O., Prikhodchenko P.V.
Inorganic Chemistry,
2022
.
Terent'ev A.O., Platonov M.M., Levitsky D.O., Dembitsky V.M.
Russian Chemical Reviews,
2011
.
Kuznetsov M.L., Rocha B.G., Pombeiro A.J., Shul’pin G.B.
ACS Catalysis,
2015
.
Ma Z., Mahmudov K.T., Aliyeva V.A., Gurbanov A.V., Guedes da Silva M.F., Pombeiro A.J.
Coordination Chemistry Reviews,
2021
.
.
Novikov A.S., Kuznetsov M.L., Pombeiro A.J., Bokach N.A., Shul’pin G.B.
ACS Catalysis,
2013
.
Rocha B.G., Kuznetsov M.L., Kozlov Y.N., Pombeiro A.J., Shul'pin G.B.
Catalysis Science and Technology,
2015
.
Novikov A.S., Kuznetsov M.L., Rocha B.G., Pombeiro A.J., Shul'pin G.B.
Catalysis Science and Technology,
2016
.
Buldashov I.A., Medvedev A.G., Mikhaylov A.A., Churakov A.V., Lev O., Prikhodchenko P.V.
CrystEngComm,
2022
.
Carmona D., Lamata M.P., Ferrer J., Modrego J., Perales M., Lahoz F.J., Atencio R., Oro L.A.
Journal of the Chemical Society Chemical Communications,
1994
.
Ellerby L.M., Cabelli D.E., Graden J.A., Valentine J.S.
Journal of the American Chemical Society,
1996
.
Root D.E., Mahroof-Tahir M., Karlin K.D., Solomon E.I.
Inorganic Chemistry,
1998
.
Guzei I.A., Bakac A.
Inorganic Chemistry,
2001
.
Rostovtsev V.V., Henling L.M., Labinger J.A., Bercaw J.E.
Inorganic Chemistry,
2002
.
Miyaji T., Kujime M., Hikichi S., Moro-oka Y., Akita M.
Inorganic Chemistry,
2002
.
Rulíšek L., Solomon E.I., Ryde U.
Inorganic Chemistry,
2005
.
Jackson T.A., Karapetian A., Miller A., Brunold T.C.
Biochemistry,
2005
.
Humphreys K.J., Mirica L.M., Wang Y., Klinman J.P.
Journal of the American Chemical Society,
2009
.
Cai X., Majumdar S., Fortman G.C., Cazin C.S., Slawin A.M., Lhermitte C., Prabhakar R., Germain M.E., Palluccio T., Nolan S.P., Rybak-Akimova E.V., Temprado M., Captain B., Hoff C.D.
Journal of the American Chemical Society,
2011
.
Teets T.S., Nocera D.G.
Journal of the American Chemical Society,
2011
.
Oloo W.N., Fielding A.J., Que L.
Journal of the American Chemical Society,
2013
.
Tamanaha E., Zhang B., Guo Y., Chang W., Barr E.W., Xing G., St. Clair J., Ye S., Neese F., Bollinger J.M., Krebs C.
Journal of the American Chemical Society,
2016
.
Palluccio T.D., Cai X., Majumdar S., Serafim L.F., Tomson N.C., Wieghardt K., Cazin C.S., Nolan S.P., Rybak-Akimova E.V., Fernández-González M.Á., Temprado M., Captain B., Hoff C.D.
Journal of the American Chemical Society,
2017
.
Mann S.I., Heinisch T., Ward T.R., Borovik A.S.
Journal of the American Chemical Society,
2017
.
Wheel-Like Icosanuclear Peroxotitanate—A Stable Water-Soluble Catalyst for Oxygen Transfer Reactions
Jin W., Yang F., Deng L., Chen M., Chen J., Chen H., Zhou Z.
Inorganic Chemistry,
2018
.
Maksimchuk N.V., Evtushok V.Y., Zalomaeva O.V., Maksimov G.M., Ivanchikova I.D., Chesalov Y.A., Eltsov I.V., Abramov P.A., Glazneva T.S., Yanshole V.V., Kholdeeva O.A., Errington R.J., Solé-Daura A., Poblet J.M., Carbó J.J., et. al.
ACS Catalysis,
2021
.
Cipriano L.A., Di Liberto G., Pacchioni G.
ACS Catalysis,
2022
.
Rettenmeier C.A., Wadepohl H., Gade L.H.
Angewandte Chemie - International Edition,
2015
.
Tsurumaki E., Sung J., Kim D., Osuka A.
Angewandte Chemie - International Edition,
2016
.
Razuvaev G.A., Brilkina T.G.
Russian Chemical Bulletin,
1975
.
Hedegård E.D., Ryde U.
Chemical Science,
2018
.
Katona G., Carpentier P., Nivière V., Amara P., Adam V., Ohana J., Tsanov N., Bourgeois D.
Science,
2007
.
Kühnel K., Derat E., Terner J., Shaik S., Schlichting I.
Proceedings of the National Academy of Sciences of the United States of America,
2007
.
Oktawiec J., Jiang H.Z., Vitillo J.G., Reed D.A., Darago L.E., Trump B.A., Bernales V., Li H., Colwell K.A., Furukawa H., Brown C.M., Gagliardi L., Long J.R.
Nature Communications,
2020
.
Wada A., Harata M., Hasegawa K., Jitsukawa K., Masuda H., Mukai M., Kitagawa T., Einaga H.
Angewandte Chemie - International Edition,
1998
.
Takahashi Y., Hashimoto M., Hikichi S., Akita M., Moro-oka Y.
Angewandte Chemie - International Edition,
1999
.
Paoli M., Liddington R., Tame J., Wilkinson A., Dodson G.
Journal of Molecular Biology,
1996
.
Denisov I.G., Makris T.M., Sligar S.G.
Journal of Biological Chemistry,
2002
.
Tejel C., Ciriano M., Jiménez S., Passarelli V., López J.
Angewandte Chemie - International Edition,
2008
.
Liu J., Ohta T., Yamaguchi S., Ogura T., Sakamoto S., Maeda Y., Naruta Y.
Angewandte Chemie - International Edition,
2009
.
Hölzl S.M., Altmann P.J., Kück J.W., Kühn F.E.
Coordination Chemistry Reviews,
2017
.
Popkov V.I., Tolstoy V.P., Nevedomskiy V.N.
Heliyon,
2019
.
Hema M.K., Karthik C.S., Lokanath N.K., Mallu P., Zarrouk A., Salih K.S., Warad I.
Journal of Molecular Liquids,
2020
.
Bakac A.
Coordination Chemistry Reviews,
2006
.
Prinčič G.G., Lozinšek M., Iskra J.
Dyes and Pigments,
2021
.
Brandes D., Blaschette A.
Journal of Organometallic Chemistry,
1974
.
Robbins M.H., Drago R.S.
Journal of Catalysis,
1997
.
Tolstoy V.P., Ehrlich A.G.
Thin Solid Films,
1997
.
.
Marikutsa A., Dobrovolskii A.A., Rumyantseva M.N., Mikhaylov A.A., Medvedev A.G., Lev O., Prikhodchenko P.V.
Journal of Alloys and Compounds,
2023
.
Takahashi Y., Hashimoto M., Hikichi S., Moro-oka Y., Akita M.
Inorganica Chimica Acta,
2004
.
Brindley P.B.
Chemistry of Functional Groups,
1983
.
Mikhaylov A.A., Medvedev A.G., Grishanov D.A., Fazliev T.M., Chernyshev V., Mel’nik E.A., Tripol’skaya T.A., Lev O., Prikhodchenko P.V.
International Journal of Molecular Sciences,
2023
.
Egorov P.A., Grishanov D.A., Medvedev A.G., Churakov A.V., Mikhaylov A.A., Ottenbacher R.V., Bryliakov K.P., Babak M.V., Lev O., Prikhodchenko P.V.
Inorganic Chemistry,
2023