Abstract
After the first structural characterization of dinuclear dinitrosyl iron complex (DNIC) in 1958 and discovery of natural dinitrosyl iron unit (DNIU) [Fe(NO)2] in 1964–1965, continued investigations on natural and synthetic DNICs explored their ubiquitous functions as (1) a product for nitrosylation of non-heme Fe proteins and chelatable iron pool, (2) a biological vehicle for iron and nitric oxide, (3) a novel redox-active unit for stabilization and activation of small molecules, (4) an electrocatalyst for water splitting, and (5) a precursor for electrodeposition of Fe-containing hybrid material. From a synthetic chemistry perspective, herein, we summarize four synthetic methodologies for preparation of structure-characterized DNICs in the attempt to attract continued development of unexplored DNICs featuring novel functions. As collected from CCDC database, structure-characterized DNICs can be classified into (1) tetrahedral {Fe(NO)2}9 DNICs with C/N/P/O/S/Se/Cl/Br/I ligation modes, (2) five-/six-coordinate {Fe(NO)2}9 DNICs with N/O ligation modes, (3) tetrahedral {Fe(NO)2}10 DNICs with C/Sn/N/P/O/S/H ligation modes, (4) metallothiolate-bound {Fe(NO)2}9/{Fe(NO)2}10 DNICs, and (5) dinuclear {Fe(NO)2}9–{Fe(NO)2}9, {Fe(NO)2}9–{Fe(NO)2}10, and {Fe(NO)2}10–{Fe(NO)2}10 DNICs with thiolate/alkoxide/pyrazolate/CO bridging ligands. After buildup of the DNIU [Fe(NO)2] using NO, NO+, and NO2− as alternative sources of nitrosyl ligands, ligand substitution and modification reaction of DNICs, redox interconversion between {Fe(NO)2}9 and {Fe(NO)2}10 cores, and transformation between mononuclear and dinuclear DNICs establish the comprehensive pathways to bridge alternative types of DNICs in the chemical library of structure-characterized DNICs. This review on the synthetic methodology for preparation of DNICs will facilitate the incorporation of DNIU [Fe(NO)2] into (bio)materials for potential applications of DNICs in chemistry, catalysis, biology, and biomedicine.
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Vanin AF, Kubrina LN, Kiladze SV, Burbaev D (1977) Biofizika 22:646–650
Vanin AF, Kiladze SV, Kubrina LN (1977) Biofizika 22:850–855
Vanin AF, Men’shikov GB, Moroz IA, Mordvintcev PI, Serezhenkov VA, Burbaev DS (1992) Biochim Biophys Acta 1135:275–279
Lancaster JR Jr, Werner-Felmayer G, Wachter H (1994) Free Radic Biol Med 16:869–870
Vanin AF (1967) Biokhimiya (Rus) 32:228–232
Vanin AF, Blumenfeld LA, Chetverikov AG (1967) Biofizika (Rus) 12:829–841
Vanin AF (1971) Biofizika (Rus) 16:650–658
Schwarz MA, Lazo JS, Yalowich JC, Allen WP, Whitmore M, Bergonia HA, Tzeng E, Billiar TR, Robbins PD, Lancaster JR Jr et al (1995) Proc Natl Acad Sci USA 92:4452–4456
Sellers VM, Johnson MK, Dailey HA (1996) Biochemistry 35:2699–2704
Kennedy MC, Antholine WE, Beinert H (1997) J Biol Chem 272:20340–20347
Cruz-Ramos H, Crack J, Wu G, Hughes MN, Scott C, Thomson AJ, Green J, Poole RK (2002) EMBO J 21:3235–3244
Rogers PA, Eide L, Klungland A, Ding H (2003) DNA Repair 2:809–817
Lewandowska H, Meczynska S, Sochanowicz B, Sadlo J, Kruszewski M (2007) J Biol Inorg Chem 12:345–352
Tinberg CE, Tonzetich ZJ, Wang H, Do LH, Yoda Y, Cramer SP, Lippard SJ (2010) J Am Chem Soc 132:18168–18176
Tonzetich ZJ, Wang H, Mitra D, Tinberg CE, Do LH, Jenney FE Jr, Adams MW, Cramer SP, Lippard SJ (2010) J Am Chem Soc 132:6914–6916
Kobayashi K (2017) Acc Chem Res 50:1672–1678
Le Brun NE, Andrews SC, Moore GR, Thomson AJ (1997) Biochem J 326:173–179
Crack JC, Stapleton MR, Green J, Thomson AJ, Le Brun NE (2013) J Biol Chem 288:11492–11502
Ding H, Demple B (2000) Proc Natl Acad Sci USA 97:5146–5150
Ren B, Zhang N, Yang J, Ding H (2008) Mol Microbiol 70:953–964
Duan X, Yang J, Ren B, Tan G, Ding H (2009) Biochem J 417:783–789
Landry AP, Duan X, Huang H, Ding H (2011) Free Radic Biol Med 50:1582–1590
Cheng Z, Landry AP, Wang Y, Ding H (2017) J Biol Chem 292:3146–3153
Foster MW, Cowan JA (1999) J Am Chem Soc 121:4093–4100
Vasil’eva SV, Stupakova MV, Lobysheva II, Mikoyan VD, Vanin AF (2001) Biochemistry 66:984–988
Pieper GM, Halligan NL, Hilton G, Konorev EA, Felix CC, Roza AM, Adams MB, Griffith OW (2003) Proc Natl Acad Sci USA 100:3125–3130
D’Autreaux B, Horner O, Oddou JL, Jeandey C, Gambarelli S, Berthomieu C, Latour JM, Michaud-Soret I (2004) J Am Chem Soc 126:6005–6016
Asanuma K, Iijima K, Ara N, Koike T, Yoshitake J, Ohara S, Shimosegawa T, Yoshimura T (2007) Nitric Oxide 16:395–402
Singh A, Guidry L, Narasimhulu KV, Mai D, Trombley J, Redding KE, Giles GI, Lancaster JR Jr, Steyn AJ (2007) Proc Natl Acad Sci USA 104:11562–11567
Strube K, de Vries S, Cramm R (2007) J Biol Chem 282:20292–20300
Yukl ET, Elbaz MA, Nakano MM, Moënne-Loccoz P (2008) Biochemistry 47:13084–13092
Hickok JR, Sahni S, Shen H, Arvind A, Antoniou C, Fung LW, Thomas DD (2011) Free Radic Biol Med 51:1558–1566
Fujikawa M, Kobayashi K, Kozawa T (2014) J Biochem 156:163–172
Grabarczyk DB, Ash PA, Vincent KA (2014) J Am Chem Soc 136:11236–11239
Severina IS, Bussygina OG, Pyatakova NV, Malenkova IV, Vanin AF (2003) Nitric Oxide 8:155–163
Mulsch A, Mordvintcev P, Vanin AF, Busse R (1991) FEBS Lett 294:252–256
Malyshev I, Malugin AV, Golubeva L, Zenina TA, Manukhina EB, Mikoyan VD, Vanin AF (1996) FEBS Lett 391:21–23
Wiegant FA, Malyshev IY, Kleschyov AL, van Faassen E, Vanin AF (1999) FEBS Lett 455:179–182
Kleschyov AL, Strand S, Schmitt S, Gottfried D, Skatchkov M, Sjakste N, Daiber A, Umansky V, Munzel T (2006) Free Radic Biol Med 40:1340–1348
Giliano NY, Konevega LV, Noskin LA, Serezhenkov VA, Poltorakov AP, Vanin AF (2011) Nitric Oxide 24:151–159
Zhukova OS, Smirnova ZS, Chikileva IO, Kiselevskii MV (2017) Bull Exp Biol Med 162:583–588
Galagan ME, Oranovskaia EV, Mordvintsev PI, Medvedev OS, Vanin AF (1988) Biull. Vsesoiuznogo Kardiol Nauchn Tsentra AMN SSSR 11:75–80
Vanin AF, Stukan RA, Manukhina EB (1996) Biochim Biophys Acta 1295:5–12
Mordvintsev PI, Putintsev MD, Galagan ME, Oranovskaia EV, Medvedev OS (1988) Biull. Vsesoiuznogo Kardiol Nauchn Tsentra AMN SSSR 11:46–51
Manukhina EB, Malyshev I, Maleniuk EB, Zenina TA, Pokidyshev DA, Mikoian VD, Kubrina LN, Vanin AF (1998) Bull Exp Biol Med 125:30–33
Vanin AF, Mokh VP, Serezhenkov VA, Chazov EI (2007) Nitric Oxide 16:322–330
Lakomkin VL, Vanin AF, Timoshin AA, Kapelko VI, Chazov EI (2007) Nitric Oxide 16:413–418
Mokh VP, Poltorakov AP, Serezhenkov VA, Vanin AF (2010) Nitric Oxide 22:266–274
Chazov EI, Rodnenkov OV, Zorin AV, Lakomkin VL, Gramovich VV, Vyborov ON, Dragnev AG, Timoshin CA, Buryachkovskaya LI, Abramov AA, Massenko VP, Arzamastsev EV, Kapelko VI, Vanin AF (2012) Nitric Oxide 26:148–156
Shekhter AB, Rudenko TG, Serezhenkov VA, Vanin AF (2007) Biofizika 52:539–547
Andreyev-Andriyevsky AA, Mikoyan VD, Serezhenkov VA, Vanin AF (2011) Nitric Oxide 24:217–223
Kuznetsov VA, Mordvintsev PI, Dank E, Iurkiv VA, Vanin AF (1988) Vopr Med Khim 34:43–46
Mordvintsev PI, Rudneva VG, Vanin AF, Shimkevich LL, Khodorov BI (1986) Biokhimiia 51:1851–1857
Watts RN, Hawkins C, Ponka P, Richardson DR (2006) Proc Natl Acad Sci USA 103:7670–7675
Lok HC, Sahni S, Richardson V, Kalinowski DS, Kovacevic Z, Lane DJ, Richardson DR (2014) Free Radic Biol Med 75:14–29
Pedersen JZ, De Maria F, Turella P, Federici G, Mattei M, Fabrini R, Dawood KF, Massimi M, Caccuri AM, Ricci G (2007) J Biol Chem 282:6364–6371
Yang W, Rogers PA, Ding H (2002) J Biol Chem 277:12868–12873
Tsai M-L, Chen C-C, Hsu I-J, Ke S-C, Hsieh C-H, Chiang K-A, Lee G-H, Wang Y, Chen J-M, Lee J-F, Liaw W-F (2004) Inorg Chem 43:5159–5167
Tsou C-C, Lin Z-S, Lu T-T, Liaw W-F (2008) J Am Chem Soc 130:17154–17160
Lu T-T, Huang H-W, Liaw W-F (2009) Inorg Chem 48:9027–9035
Fitzpatrick J, Kim E (2015) Acc Chem Res 48:2453–2461
Tran CT, Kim E (2012) Inorg Chem 51:10086–10088
Fitzpatrick J, Kalyvas H, Filipovic MR, Ivanovic-Burmazovic I, MacDonald JC, Shearer J, Kim E (2014) J Am Chem Soc 136:7229–7232
Ke C-H, Chen C-H, Tsai M-L, Wang H-C, Tsai F-T, Chiang Y-W, Shih W-C, Bohle SD, Liaw W-F (2017) J Am Chem Soc 139:67–70
Tsou C-C, Tsai F-T, Chen H-Y, Hsu I-J, Liaw W-F (2013) Inorg Chem 52:1631–1639
Tsou C-C, Chiu W-C, Ke C-H, Tsai J-C, Wang Y-M, Chiang M-H, Liaw W-F (2014) J Am Chem Soc 136:9424–9433
Tsai F-T, Kuo T-S, Liaw W-F (2009) J Am Chem Soc 131:3426–3427
Tsai F-T, Chen P-L, Liaw W-F (2010) J Am Chem Soc 132:5290–5299
Tsai F-T, Lee Y-C, Chiang M-H, Liaw W-F (2013) Inorg Chem 52:464–473
Hsieh C-H, Ding S, Erdem OF, Crouthers DJ, Liu T, McCrory CC, Lubitz W, Popescu CV, Reibenspies JH, Hall MB, Darensbourg MY (2014) Nat Commun 5:3684
Ding S, Ghosh P, Lunsford AM, Wang N, Bhuvanesh N, Hall MB, Darensbourg MY (2016) J Am Chem Soc 138:12920–12927
Ding S, Ghosh P, Darensbourg MY, Hall MB (2017) Proc Natl Acad Sci USA 114:E9775–E9782
Ghosh P, Ding SD, Chupik RB, Quiroz M, Hsieh CH, Bhuvanesh N, Hall MB, Darensbourg MY (2017) Chem Sci 8:8291–8300
Chiou T-W, Lu T-T, Wu Y-H, Yu Y-J, Chu L-K, Liaw W-F (2015) Angew Chem 54:14824–14829
Li W-L, Chiou T-W, Chen C-H, Yu Y-J, Chu L-K, Liaw W-F (2018) Dalton Trans 47:7128–7134
Ke C-H, Shih W-C, Tsai F-T, Tsai M-L, Ching W-M, Hsieh H-H, Liaw W-F (2018) Inorg Chem 57:14715–14726
Butler AR, Flitney FW, Williams DL (1995) Trends Pharmacol Sci 16:18–22
Ueno T, Yoshimura T (2000) Jpn J Pharmacol 82:95–101
Vanin AF, Burbaev D (2011) J Biophys 2011:878236
Lewandowska H, Kalinowska M, Brzoska K, Wojciuk K, Wojciuk G, Kruszewski M (2011) Dalton Trans 40:8273–8289
Pulukkody R, Darensbourg MY (2015) Acc Chem Res 48:2049–2058
Tsai M-L, Tsou C-C, Liaw W-F (2015) Acc Chem Res 48:1184–1193
Li L, Li L (2016) Coord Chem Rev 306:678–700
Kovacevic Z, Sahni S, Lok H, Davies MJ, Wink DA, Richardson DR (2017) Biochim Biophys Acta 1861:995–999
Vanin AF (2018) Cell Biochem Biophys 76:3–17
Vanin AF (2016) Nitric Oxide 54:15–29
Denny JA, Darensbourg MY (2015) Chem Rev 115:5248–5273
Lu T-T, Wang Y-M, Hung C-H, Chiou S-J, Liaw W-F (2018) Inorg Chem 57:12425–12443
Hsiao H-Y, Chung C-W, Santos JH, Villaflores OB, Lu T-T (2019) Dalton Trans Adv Article
Harrop TC, Song D, Lippard SJ (2006) J Am Chem Soc 128:3528–3529
Lu T-T, Chiou S-J, Chen C-Y, Liaw W-F (2006) Inorg Chem 45:8799–8806
Tsou C-C, Lu T-T, Liaw W-F (2007) J Am Chem Soc 129:12626–12627
Thomas JT, Robertson JH, Cox EG (1958) Acta Crystallogr 11:599–604
Rudneva TN, Sanina NA, Lyssenko KA, Aldoshin SM, Yu Antipinb M, Ovanesyana NS (2009) Mendeleevsk Commun 19:253–255
Davidovich PB, Gurzhiy VV, Garabadzhiu AV, Belyaeva AN (2015) Russ Chem Bull 64:2663–2666
Glidewell C, Lambert RJ, Hursthouse MB, Motevalli M (1989) Datlon Trans. https://doi.org/10.1039/DT9890002061
Sanina NA, Aldoshin SM, Shmatko NY, Korchagin DV, Shilov GV, Knyazkina EV, Ovanesyan NS, Kulikov AV (2015) New J Chem 39:1022–1030
Shmatko NY, Korchagin DV, Shilov GV, Sanina NA, Aldoshin SM (2017) J Struct Chem 58:353–355
Shmatko NY, Korchagin DV, Shilov GV, Ovanesyan NS, Kulikov AV, Sanina NA, Aldoshin SM (2017) Polyhedron 137:72–80
Harrop TC, Song D, Lippard SJ (2007) J Inorg Biochem 101:1730–1738
Harrop TC, Tonzetich ZJ, Reisner E, Lippard SJ (2008) J Am Chem Soc 130:15602–15610
Tonzetich ZJ, Do LH, Lippard SJ (2009) J Am Chem Soc 131:7964–7965
Tran CT, Williard PG, Kim E (2014) J Am Chem Soc 136:11874–11877
Schiewer CE, Muller CS, Dechert S, Bergner M, Wolny JA, Schunemann V, Meyer F (2018) Inorg Chem 58:769–784
Speelman AL, Zhang B, Silakovi A, Skodje KM, Alp EE, Zhao J, Hu MY, Kim E, Krebs C, Lehnert N (2016) Inorg Chem 55:5485–5501
Jo DH, Chiou YM, Que L (2001) Inorg Chem 40:3181–3190
Kisko JL, Hascall T, Parkin G (1998) J Am Chem Soc 120:10561–10562
Mazany AM, Fackler JP, Gallagher MK (1983) Inorg Chem 22:2593–2596
Bottcher HC, Mayer P, Mayer T (2013) Z Anorg Allg Chem 639:2609–2611
Stevens RE, Gladfelter WL (1983) Inorg Chem 22:2034–2042
Connelly NG, Gardner C (1976) Dalton Trans. https://doi.org/10.1039/DT9760001525
Kwon YM, Delgado M, Zakharov LN, Seda T, Gilbertson JD (2016) Chem Commun 52:11016–11019
Burns KT, Marks WR, Cheung PM, Seda T, Zakharov LN, Gilbertson JD (2018) Inorg Chem 57:9601–9610
Lee H-M, Chiou S-J (2009) Acta Crystallogr E 65:M1600-U1925
Liaw W-F, Chiang CY, Lee GH, Peng SM, Lai CH, Darensbourg MY (2000) Inorg Chem 39:480–484
Wang R, Wang X, Sundberg EB, Nguyen P, Grant GP, Sheth C, Zhao Q, Herron S, Kantardjieff KA, Li L (2009) Inorg Chem 48:9779–9785
Hung M-C, Tsai M-C, Lee G-H, Liaw W-F (2006) Inorg Chem 45:6041–6047
Reginato N, McCrory CTC, Pervitsky D, Li L (1999) J Am Chem Soc 121:10217–10218
Dillinger SAT, Schmalle HW, Fox T, Berke H (2007) Dalton Trans. https://doi.org/10.1039/B702461D
Holloway LR, Clough AJ, Li JY, Tao EL, Tao FM, Li L (2014) Polyhedron 70:29–38
Jones MW, Powell DR, Richter-Addo GB (2014) J Organomet Chem 754:63–74
Jones MW, Powell DR, Richter-Addo GB (2011) Acta Crystallogr E 67:m247
Jones MW, Powell DR, Richter-Addo GB (2011) Acta Crystallogr E 67:m332
Jones MW, Powell DR, Richter-Addo GB (2011) Acta Crystallogr E 67:m331
Wittkamp F, Nagel C, Lauterjung P, Mallick B, Schatzschneider U, Apfel UP (2016) Dalton Trans 45:10271–10279
Li L, Reginato N, Urschey M, Stradiotto M, Liarakos JD (2003) Can J Chem 81:468–475
Weidenbruch M, Stilter A, Saak W, Peters K, Schnering HGV (1998) J Organomet Chem 560:125–129
Horsken A, Zheng G, Stradiotto M, McCrory CTC, Li L (1998) J Organomet Chem 558:1–9
Osterloh F, Saak W, Haase D, Pohl S (1997) Chem Commun. https://doi.org/10.1039/A700884H
Ghosh P, Quiroz M, Pulukkody R, Bhuvanesh N, Darensbourg MY (2018) Dalton Trans 47:11812–11819
Chen H-W, Lin C-W, Chen C-C, Yang L-B, Chiang M-H, Liaw W-F (2005) Inorg Chem 44:3226–3232
Hsieh C-H, Chupik RB, Brothers SM, Hall MB, Darensbourg MY (2011) Dalton Trans 40:6047–6053
Albano VG, Araneo A, Bellon PL, Ciani G, Manassero M (1974) J Organomet Chem 67:413–422
Tsai M-L, Hsieh C-H, Liaw W-F (2007) Inorg Chem 46:5110–5117
Wang R, Xu W, Zhang J, Li L (2009) J Mol Struct 923:110–113
Chen Y-J, Ku W-C, Feng L-T, Tsai M-L, Hsieh C-H, Hsu W-H, Liaw W-F, Hung C-H, Chen Y-J (2008) J Am Chem Soc 130:10929–10938
Wang R, Camacho-Fernandez MA, Xu W, Zhang J, Li L (2009) Dalton Trans. https://doi.org/10.1039/B810230A
Tsou C-C, Liaw W-F (2011) Chem Eur J 17:13358–13366
Pulukkody R, Chupik RB, Montalvo SK, Khan S, Bhuvanesh N, Lim SM, Darensbourg MY (2017) Chem Commun 53:1180–1183
Keller E, Vahrenkamp H (1979) Chem Ber 112:1626–1634
Tseng Y-T, Chen C-H, Lin J-Y, Li B-H, Lu Y-H, Lin C-H, Chen H-T, Weng T-C, Sokaras D, Chen H-Y, Soo Y-L, Lu T-T (2015) Chem Eur J 21:17570–17573
Chong KS, Rettig SJ, Storr A, Trotter J (1979) Can J Chem 57:3119–3125
Lu C-Y, Liaw W-F (2013) Inorg Chem 52:13918–13926
Lo F-C, Li Y-W, Hsu I-J, Chen C-H, Liaw W-F (2014) Inorg Chem. 53:10881–10892
Chen C-H, Chiou S-J, Chen H-Y (2010) Inorg Chem 49:2023–2025
Yeh S-W, Lin C-W, Liu B-H, Tsou C-C, Tsai M-L, Liaw W-F (2015) Chem Eur J 21:16035–16046
Lo F-C, Ho Y-C, Chang P-Y, Lee G-H, Kuo T-S, Chen J-L, Chen C-H (2014) Eur J Inorg Chem 2014:3499–3509
Huang H-C, Ching W-M, Tseng Y-T, Chen C-H, Lu T-T (2019) Dalton Trans. https://doi.org/10.1039/C9DT00777F
Wang J-H, Chen C-H (2010) Inorg Chem 49:7644–7646
Baltusis LM, Karlin KD, Rabinowitz HN, Dewan JC, Lippard SJ (1980) Inorg Chem 19:2627–2632
Chiang C-Y, Miller ML, Reibenspies JH, Darensbourg MY (2004) J Am Chem Soc 126:10867–10874
Atkinson FL, Blackwell HE, Brown NC, Connelly NG, Crossley JG, Orpen AG, Rieger AL, Rieger PH (1996) Dalton Trans. https://doi.org/10.1039/DT9960003491
Sanina NA, Rakova OA, Aldoshin SM, Shilov GV, Shulga YM, Kulikov AV, Ovanesyan NS (2004) Mendeleevsk Commun 14:7–8
Sanina NA, Aldoshin SM, Rudneva TN, Golovina NI, Shilov GV, Shulga YM, Ovanesyan NS, Ikorskiy VN, Ovcharenko VI (2005) J Mol Struct 752:110–114
Sanina N, Roudneva T, Shilov G, Morgunov R, Ovanesyan N, Aldoshin S (2009) Dalton Trans. https://doi.org/10.1039/B818443G
Sanina NA, Kozub GI, Kondrat’eva TA, Shilov GV, Korchagin DV, Emel’yanova NS, Poleshchuk OK, Chernyak AV, Kulikov AV, Mushenok FB, Ovanesyan NS, Aldoshin SM (2013) J Mol Struct 1041:183–189
Sanina NA, Kozub GI, Kondratéva TA, Korchagin DV, Shilov GV, Anova NSE, Manzhos RA, Krivenko AG, Aldoshin SM (2014) J Mol Struct 1075:159–165
Sanina NA, Krivenko AG, Manzhos RA, Emel’yanova NS, Kozub GI, Korchagin DV, Shilov GV, Kondrat’eva TA, Ovanesyan NS, Aldoshin SM (2014) New J Chem 38:292–301
Rakova OA, Sanina NA, Aldoshin SM, Goncharova NV, Shilov GV, Shulga YM, Ovanesyan NS (2003) Inorg. Chem Commun 6:145–148
Sanina NA, Rudneva TN, Aldoshin SM, Shilov GV, Kortchagin DV, Shul’ga YM, Martynenko VM, Ovanesyan NS (2006) Inorg Chim Acta 359:570–576
Sanina NA, Kozub GI, Zhukova OS, Emel’yanova NS, Kondrat’eva TA, Korchagin DV, Shilov GV, Ovanesyan NS, Aldoshin SM (2013) J Coord Chem 66:3602–3618
Hess JL, Hsieh C-H, Reibenspies JH, Darensbourg MY (2011) Inorg Chem 50:8541–8552
Pulukkody R, Kyran SJ, Bethel RD, Hsieh CH, Hall MB, Darensbourg DJ, Darensbourg MY (2013) J Am Chem Soc 135:8423–8430
Pulukkody R, Kyran SJ, Drummond MJ, Hsieh C-H, Darensbourg DJ, Darensbourg MY (2014) Chem Sci 5:3795–3802
Chen C-H, Ho Y-C, Lee G-H (2009) J Organomet Chem 694:3395–3400
Pinder TA, Montalvo SK, Hsieh CH, Lunsford AM, Bethel RD, Pierce BS, Darensbourg MY (2014) Inorg Chem 53:9095–9105
Davies SC, Evans DJ, Hughes DL, Konkol M, Richards RL, Sanders JR, Sobota P (2002) Dalton Trans. https://doi.org/10.1039/B200694B
Chong KS, Rettig SJ, Storr A, Trotter J (1979) Can J Chem 57:3113–3118
Tsai F-T, Chiou S-J, Tsai M-C, Huang H-W, Chiang M-H, Liaw W-F (2005) Inorg Chem 44:5872–5881
Tsai M-C, Tsai F-T, Lu T-T, Tsai M-L, Wei Y-C, Hsu I-J, Lee J-F, Liaw W-F (2009) Inorg Chem 48:9579–9591
Hsieh C-H, Brothers SM, Reibenspies JH, Hall MB, Popescu CV, Darensbourg MY (2013) Inorg Chem 52:2119–2124
Liu P-H, Tsai F-T, Chen B-H, Hsu I-J, Hsieh H-H, Liaw W-F (2019) Dalton Trans Adv Article 48:6040–6050
Huang H-W, Tsou C-C, Kuo T-S, Liaw W-F (2008) Inorg Chem 47:2196–2204
Lu T-T, Chen C-H, Liaw W-F (2010) Chem Eur J 16:8088–8095
Li L, Enright GD, Preston KF (1994) Organometallics 13:4686–4688
Hsieh C-H, Pulukkody R, Darensbourg MY (2013) Chem Commun 49:9326–9328
Hsieh C-H, Darensbourg MY (2010) J Am Chem Soc 132:14118–14125
Hsieh C-H, Chupik RB, Pinder TA, Darensbourg MY (2013) Polyhedron 58:151–155
Ghosh P, Ding S, Quiroz M, Bhuvanesh N, Hsieh CH, Palacios PM, Pierce BS, Darensbourg MY, Hall MB (2018) Chem Eur J 24:16003–16008
Lin Z-S, Lo F-C, Li C-H, Chen C-H, Huang W-N, Hsu I-J, Lee J-F, Horng J-C, Liaw W-F (2011) Inorg Chem 50:10417–10431
Kozub GI, Sanina NA, Emel’yanova NS, Utenishev AN, Kondrat’eva TA, Khrustalev VN, Ovanesyan NS, Kupchinskaya NE, Aldoshina SM (2018) Inorg Chim Acta 480:132–139
Mak TCW (1983) Inorg Chim Acta 73:159–164
Davidovich PB, Gurzhy VV, Belyaev AN (2014) Russ J Gen Chem 84:719–721
Atkinson FL, Brown NC, Connelly NG, Orpen AG, Rieger AL, Rieger PH, Rosair GM (1996) Dalton Trans. https://doi.org/10.1039/DT9960001959
Lu T-T, Tsou C-C, Huang H-W, Hsu I-J, Chen J-M, Kuo T-S, Wang Y, Liaw W-F (2008) Inorg Chem 47:6040–6050
Yeh S-W, Lin C-W, Li Y-W, Hsu I-J, Chen C-H, Jang L-Y, Lee J-F, Liaw W-F (2012) Inorg Chem 51:4076–4087
Lu T-T, Lai S-H, Li Y-W, Hsu I-J, Jang L-Y, Lee J-F, Chen I-C, Liaw W-F (2011) Inorg Chem 50:5396–5406
Chiou S-J, Wang C-C, Chang C-M (2008) J Organomet Chem 693:3582–3586
Wu S-C, Lu C-Y, Chen Y-L, Lo F-C, Wang T-Y, Chen Y-J, Yuan S-S, Liaw W-F, Wang Y-M (2016) Inorg Chem 55:9383–9392
Tsai M-L, Liaw W-F (2006) Inorg Chem 45:6583–6585
Wah HLK, Postel M, Pierrot M (1989) Inorg Chim Acta 165:215–220
Munyejabo V, Damiano J, Postel M, Bensimon C, Roustan JL (1995) J Organomet Chem 491:61–69
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We gratefully acknowledge the Ministry of Science and Technology (Taiwan) for financial support.
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Cho, SL., Liao, CJ. & Lu, TT. Synthetic methodology for preparation of dinitrosyl iron complexes. J Biol Inorg Chem 24, 495–515 (2019). https://doi.org/10.1007/s00775-019-01668-z
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DOI: https://doi.org/10.1007/s00775-019-01668-z