Solvent Similarity Index

Home , Dihydrolevoglucosenone, Ethyl phenyl ether, Sulfolane

Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is © the Owner Societies 2020

Solvent similarity index.

Mark Driver,a and Christopher A. Hunter∗a a Department of Chemistry, University of Cambridge, Lensﬁeld Road, Cambridge CB2 1EW, UK. Tel: +44 (0)1223 336710; E-mail: [email protected]

Supplementary Information

S1 SSIP domain normalisation factors S1

S2 Pure solvent information S1

S3 Similarity regional dendrograms S6

S1 SSIP domain normalisation factors

−1 Domain ηj/kJmol −10.0 ≤ i < −5.0 29.574 −5.0 ≤ i < −2.0 9.880 −2.0 ≤ i < 0.0 2.111 0.0 ≤ i < 1.0 2.069 1.0 ≤ i < 3.0 11.245 3.0 ≤ i < 5.0 30.556

Table S1: Normalisation factors for SSIP domains.

S2 Pure solvent information

Solvent ID InChIKey tetramethylsilane 1 CZDYPVPMEAXLPK-UHFFFAOYSA-N n-pentane 2 OFBQJSOFQDEBGM-UHFFFAOYSA-N 2-methylbutane 3 QWTDNUCVQCZILF-UHFFFAOYSA-N n-hexane 4 VLKZOEOYAKHREP-UHFFFAOYSA-N cyclohexane 5 XDTMQSROBMDMFD-UHFFFAOYSA-N n-heptane 6 IMNFDUFMRHMDMM-UHFFFAOYSA-N n-octane 7 TVMXDCGIABBOFY-UHFFFAOYSA-N 2,2,4-trimethylpentane 8 NHTMVDHEPJAVLT-UHFFFAOYSA-N n-decane 9 DIOQZVSQGTUSAI-UHFFFAOYSA-N n-dodecane 10 SNRUBQQJIBEYMU-UHFFFAOYSA-N n-hexadecane 11 DCAYPVUWAIABOU-UHFFFAOYSA-N benzene 12 UHOVQNZJYSORNB-UHFFFAOYSA-N toluene 13 YXFVVABEGXRONW-UHFFFAOYSA-N ortho-xylene 14 CTQNGGLPUBDAKN-UHFFFAOYSA-N meta-xylene 15 IVSZLXZYQVIEFR-UHFFFAOYSA-N para-xylene 16 URLKBWYHVLBVBO-UHFFFAOYSA-N ethylbenzene 17 YNQLUTRBYVCPMQ-UHFFFAOYSA-N isopropylbenzene 18 RWGFKTVRMDUZSP-UHFFFAOYSA-N 1,3,5-trimethylbenzene 19 AUHZEENZYGFFBQ-UHFFFAOYSA-N styrene 20 PPBRXRYQALVLMV-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene 21 CXWXQJXEFPUFDZ-UHFFFAOYSA-N cis-decalin 22 NNBZCPXTIHJBJL-AOOOYVTPSA-N Continued on next page

S1 Solvent ID InChIKey water 23 XLYOFNOQVPJJNP-UHFFFAOYSA-N methanol 24 OKKJLVBELUTLKV-UHFFFAOYSA-N ethanol 25 LFQSCWFLJHTTHZ-UHFFFAOYSA-N 1-propanol 26 BDERNNFJNOPAEC-UHFFFAOYSA-N 2-propanol 27 KFZMGEQAYNKOFK-UHFFFAOYSA-N 1-butanol 28 LRHPLDYGYMQRHN-UHFFFAOYSA-N 2-methyl-1-propanol 29 ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 2-butanol 30 BTANRVKWQNVYAZ-BYPYZUCNSA-N 2-methyl-2-propanol 31 DKGAVHZHDRPRBM-UHFFFAOYSA-N 1-pentanol 32 AMQJEAYHLZJPGS-UHFFFAOYSA-N 3-methyl-1-butanol 33 PHTQWCKDNZKARW-UHFFFAOYSA-N 2-methyl-2-butanol 34 MSXVEPNJUHWQHW-UHFFFAOYSA-N 1-hexanol 35 ZSIAUFGUXNUGDI-UHFFFAOYSA-N cyclohexanol 36 HPXRVTGHNJAIIH-UHFFFAOYSA-N 1-octanol 37 KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-decanol 38 MWKFXSUHUHTGQN-UHFFFAOYSA-N 1-dodecanol 39 LQZZUXJYWNFBMV-UHFFFAOYSA-N benzyl alcohol 40 WVDDGKGOMKODPV-UHFFFAOYSA-N 2-phenylethanol 41 WRMNZCZEMHIOCP-UHFFFAOYSA-N allyl alcohol 42 XXROGKLTLUQVRX-UHFFFAOYSA-N 2-chloroethanol 43 SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-cyanoethanol 44 WSGYTJNNHPZFKR-UHFFFAOYSA-N 2,2,2-triﬂuoroethanol 45 RHQDFWAXVIIEBN-UHFFFAOYSA-N 1,1,1,3,3,3-hexaﬂuoro-2-propanol 46 BYEAHWXPCBROCE-UHFFFAOYSA-N 2-methoxyethanol 47 XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-ethoxyethanol 48 ZNQVEEAIQZEUHB-UHFFFAOYSA-N ethylene glycol 49 LYCAIKOWRPUZTN-UHFFFAOYSA-N 1,2-propanediol 50 DNIAPMSPPWPWGF-GSVOUGTGSA-N 1,3-propanediol 51 YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,2-butanediol 52 BMRWNKZVCUKKSR-SCSAIBSYSA-N (2R,3S)-2,3-butanediol 53 OWBTYPJTUOEWEK-ZXZARUISSA-N 1,4-butanediol 54 WERYXYBDKMZEQL-UHFFFAOYSA-N 1,5-pentanediol 55 ALQSHHUCVQOPAS-UHFFFAOYSA-N diethylene glycol 56 MTHSVFCYNBDYFN-UHFFFAOYSA-N triethylene glycol 57 ZIBGPFATKBEMQZ-UHFFFAOYSA-N glycerol 58 PEDCQBHIVMGVHV-UHFFFAOYSA-N phenol 59 ISWSIDIOOBJBQZ-UHFFFAOYSA-N ortho-cresol 60 QWVGKYWNOKOFNN-UHFFFAOYSA-N meta-cresol 61 RLSSMJSEOOYNOY-UHFFFAOYSA-N para-cresol 62 IWDCLRJOBJJRNH-UHFFFAOYSA-N 2-methoxyphenol 63 LHGVFZTZFXWLCP-UHFFFAOYSA-N 2,4-dimethylphenol 64 KUFFULVDNCHOFZ-UHFFFAOYSA-N 3-chlorophenol 65 HORNXRXVQWOLPJ-UHFFFAOYSA-N diethyl ether 66 RTZKZFJDLAIYFH-UHFFFAOYSA-N di-n-propyl ether 67 POLCUAVZOMRGSN-UHFFFAOYSA-N diisopropyl ether 68 ZAFNJMIOTHYJRJ-UHFFFAOYSA-N dibutyl ether 69 DURPTKYDGMDSBL-UHFFFAOYSA-N bis(2-chloroethyl) ether 70 ZNSMNVMLTJELDZ-UHFFFAOYSA-N 1,2-dimethyoxyethane 71 XTHFKEDIFFGKHM-UHFFFAOYSA-N diethylene glycol dimethyl ether 72 SBZXBUIDTXKZTM-UHFFFAOYSA-N furan 73 YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran 74 WYURNTSHIVDZCO-UHFFFAOYSA-N 2-methyltetrahydrofuran 75 JWUJQDFVADABEY-RXMQYKEDSA-N tetrahydropyran 76 DHXVGJBLRPWPCS-UHFFFAOYSA-N 1,3-dioxane 77 VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxolan 78 WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,8-cineole 79 WEEGYLXZBRQIMU-WAAGHKOSSA-N anisole 80 RDOXTESZEPMUJZ-UHFFFAOYSA-N ethyl phenyl ether 81 DLRJIFUOBPOJNS-UHFFFAOYSA-N diphenyl ether 82 USIUVYZYUHIAEV-UHFFFAOYSA-N dibenzyl ether 83 MHDVGSVTJDSBDK-UHFFFAOYSA-N 1,2-dimethoxybenzene 84 ABDKAPXRBAPSQN-UHFFFAOYSA-N methyl orthoformate 85 PYOKUURKVVELLB-UHFFFAOYSA-N Continued on next page

S2 Solvent ID InChIKey methyl orthoacetate 86 HDPNBNXLBDFELL-UHFFFAOYSA-N propionaldehyde 87 NBBJYMSMWIIQGU-UHFFFAOYSA-N butyraldehyde 88 ZTQSAGDEMFDKMZ-UHFFFAOYSA-N benzaldehyde 89 HUMNYLRZRPPJDN-UHFFFAOYSA-N p-methoxybenzaldehyde 90 ZRSNZINYAWTAHE-UHFFFAOYSA-N cinnamaldehyde 91 KJPRLNWUNMBNBZ-QPJJXVBHSA-N acetone 92 CSCPPACGZOOCGX-UHFFFAOYSA-N 2-butanone 93 ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-pentanone 94 XNLICIUVMPYHGG-UHFFFAOYSA-N 3-methyl-2-butanone 95 SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-pentanone 96 FDPIMTJIUBPUKL-UHFFFAOYSA-N cyclopentanone 97 BGTOWKSIORTVQH-UHFFFAOYSA-N 4-methyl-2-pentanone 98 NTIZESTWPVYFNL-UHFFFAOYSA-N 3,3-dimethyl-2-butanone 99 PJGSXYOJTGTZAV-UHFFFAOYSA-N perfluorooctane 100 YVBBRRALBYAZBM-UHFFFAOYSA-N cyclohexanone 101 JHIVVAPYMSGYDF-UHFFFAOYSA-N 2-heptanone 102 CATSNJVOTSVZJV-UHFFFAOYSA-N 3-heptanone 103 NGAZZOYFWWSOGK-UHFFFAOYSA-N 2,2,4,4-tetramethyl-3-pentanone 104 UIQGEWJEWJMQSL-UHFFFAOYSA-N acetophenone 105 KWOLFJPFCHCOCG-UHFFFAOYSA-N ethyl phenyl ketone 106 KRIOVPPHQSLHCZ-UHFFFAOYSA-N benzyl methyl ketone 107 QCCDLTOVEPVEJK-UHFFFAOYSA-N 2,4,5-trimethylacetophenone 108 GENBEGZNCBFHSU-UHFFFAOYSA-N p-chloroacetophenone 109 BUZYGTVTZYSBCU-UHFFFAOYSA-N diphenyl ketone 110 RWCCWEUUXYIKHB-UHFFFAOYSA-N 2,4-pentanedione 111 YRKCREAYFQTBPV-UHFFFAOYSA-N 2,3-butanedione 112 QSJXEFYPDANLFS-UHFFFAOYSA-N formic acid 113 BDAGIHXWWSANSR-UHFFFAOYSA-N acetic acid 114 QTBSBXVTEAMEQO-UHFFFAOYSA-N propanoic acid 115 XBDQKXXYIPTUBI-UHFFFAOYSA-N butanoic acid 116 FERIUCNNQQJTOY-UHFFFAOYSA-N pentanoic acid 117 NQPDZGIKBAWPEJ-UHFFFAOYSA-N hexanoic acid 118 FUZZWVXGSFPDMH-UHFFFAOYSA-N heptanoic acid 119 MNWFXJYAOYHMED-UHFFFAOYSA-N dichloroacetic acid 120 JXTHNDFMNIQAHM-UHFFFAOYSA-N trifluoroacetic acid 121 DTQVDTLACAAQTR-UHFFFAOYSA-N acetic anhydride 122 WFDIJRYMOXRFFG-UHFFFAOYSA-N benzoyl chloride 123 PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl bromide 124 AQIHMSVIAGNIDM-UHFFFAOYSA-N methyl formate 125 TZIHFWKZFHZASV-UHFFFAOYSA-N ethyl formate 126 WBJINCZRORDGAQ-UHFFFAOYSA-N methyl acetate 127 KXKVLQRXCPHEJC-UHFFFAOYSA-N ethyl acetate 128 XEKOWRVHYACXOJ-UHFFFAOYSA-N n-propyl acetate 129 YKYONYBAUNKHLG-UHFFFAOYSA-N butyl acetate 130 DKPFZGUDAPQIHT-UHFFFAOYSA-N isopentyl acetate 131 MLFHJEHSLIIPHL-UHFFFAOYSA-N methyl propionate 132 RJUFJBKOKNCXHH-UHFFFAOYSA-N ethyl propionate 133 FKRCODPIKNYEAC-UHFFFAOYSA-N dimethyl carbonate 134 IEJIGPNLZYLLBP-UHFFFAOYSA-N diethyl carbonate 135 OIFBSDVPJOWBCH-UHFFFAOYSA-N ethylene carbonate 136 KMTRUDSVKNLOMY-UHFFFAOYSA-N 4-methyl-1,3-dioxolan-2-one 137 RUOJZAUFBMNUDX-GSVOUGTGSA-N diethyl malonate 138 IYXGSMUGOJNHAZ-UHFFFAOYSA-N methyl benzoate 139 QPJVMBTYPHYUOC-UHFFFAOYSA-N ethyl benzoate 140 MTZQAGJQAFMTAQ-UHFFFAOYSA-N dimethylphthalate 141 NIQCNGHVCWTJSM-UHFFFAOYSA-N di-n-butylorthophthalate 142 DOIRQSBPFJWKBE-UHFFFAOYSA-N ethyl chloroacetate 143 VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl trichloroacetate 144 SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl acetoacetate 145 XYIBRDXRRQCHLP-UHFFFAOYSA-N gamma-butyrolactone 146 YEJRWHAVMIAJKC-UHFFFAOYSA-N n-perfluorohexane 147 ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluoromethylcyclohexane 148 QIROQPWSJUXOJC-UHFFFAOYSA-N Continued on next page

S3 Solvent ID InChIKey perfluoroheptane 149 LGUZHRODIJCVOC-UHFFFAOYSA-N cis-perfluorodecalin 150 UWEYRJFJVCLAGH-XIXRPRMCSA-N fluorobenzene 151 PYLWMHQQBFSUBP-UHFFFAOYSA-N hexafluorobenzene 152 ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 1,4-dichlorobutane 153 KJDRSWPQXHESDQ-UHFFFAOYSA-N chlorobenzene 154 MVPPADPHJFYWMZ-UHFFFAOYSA-N dichloromethane 155 YMWUJEATGCHHMB-UHFFFAOYSA-N 1,1-dichloroethane 156 SCYULBFZEHDVBN-UHFFFAOYSA-N 1,2-dichloroethane 157 WSLDOOZREJYCGB-UHFFFAOYSA-N trans-1,2-dichloroethylene 158 KFUSEUYYWQURPO-OWOJBTEDSA-N ortho-dichlorobenzene 159 RFFLAFLAYFXFSW-UHFFFAOYSA-N meta-dichlorobenzene 160 ZPQOPVIELGIULI-UHFFFAOYSA-N chloroform 161 HEDRZPFGACZZDS-UHFFFAOYSA-N 1,1,1-trichloroethane 162 UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,2-trichloroethane 163 UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene 164 XSTXAVWGXDQKEL-UHFFFAOYSA-N 1,2,4-trichlorobenzene 165 PBKONEOXTCPAFI-UHFFFAOYSA-N carbon tetrachloride 166 VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloroethylene 167 CYTYCFOTNPOANT-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane 168 QPFMBZIOSGYJDE-UHFFFAOYSA-N pentachloroethane 169 BNIXVQGCZULYKV-UHFFFAOYSA-N 1-bromobutane 170 MPPPKRYCTPRNTB-UHFFFAOYSA-N bromobenzene 171 QARVLSVVCXYDNA-UHFFFAOYSA-N dibromomethane 172 FJBFPHVGVWTDIP-UHFFFAOYSA-N 1,2-dibromoethane 173 PAAZPARNPHGIKF-UHFFFAOYSA-N bromoform 174 DIKBFYAXUHHXCS-UHFFFAOYSA-N n-butyl iodide 175 KMGBZBJJOKUPIA-UHFFFAOYSA-N iodobenzene 176 SNHMUERNLJLMHN-UHFFFAOYSA-N methylene iodide 177 NZZFYRREKKOMAT-UHFFFAOYSA-N n-butylamine 178 HQABUPZFAYXKJW-UHFFFAOYSA-N benzylamine 179 WGQKYBSKWIADBV-UHFFFAOYSA-N ethylenediamine 180 PIICEJLVQHRZGT-UHFFFAOYSA-N diethylamine 181 HPNMFZURTQLUMO-UHFFFAOYSA-N di-n-butylamine 182 JQVDAXLFBXTEQA-UHFFFAOYSA-N pyrrole 183 KAESVJOAVNADME-UHFFFAOYSA-N pyrrolidine 184 RWRDLPDLKQPQOW-UHFFFAOYSA-N piperidine 185 NQRYJNQNLNOLGT-UHFFFAOYSA-N morpholine 186 YNAVUWVOSKDBBP-UHFFFAOYSA-N triethylamine 187 ZMANZCXQSJIPKH-UHFFFAOYSA-N tri-(n-butyl)amine 188 IMFACGCPASFAPR-UHFFFAOYSA-N aniline 189 PAYRUJLWNCNPSJ-UHFFFAOYSA-N o-chloroaniline 190 AKCRQHGQIJBRMN-UHFFFAOYSA-N methylphenylamine 191 AFBPFSWMIHJQDM-UHFFFAOYSA-N N,N-dimethylaniline 192 JLTDJTHDQAWBAV-UHFFFAOYSA-N aminoethanol 193 HZAXFHJVJLSVMW-UHFFFAOYSA-N diethanolamine 194 ZBCBWPMODOFKDW-UHFFFAOYSA-N triethanolamine 195 GSEJCLTVZPLZKY-UHFFFAOYSA-N pyridine 196 JUJWROOIHBZHMG-UHFFFAOYSA-N 2-methylpyridine 197 BSKHPKMHTQYZBB-UHFFFAOYSA-N 3-methylpyridine 198 ITQTTZVARXURQS-UHFFFAOYSA-N 4-methylpyridine 199 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 2,4-dimethylpyridine 200 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,6-dimethylpyridine 201 OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,4,6-trimethylpyridine 202 BWZVCCNYKMEVEX-UHFFFAOYSA-N 2-bromopyridine 203 IMRWILPUOVGIMU-UHFFFAOYSA-N 3-bromopyridine 204 NYPYPOZNGOXYSU-UHFFFAOYSA-N 2-cyanopyridine 205 FFNVQNRYTPFDDP-UHFFFAOYSA-N pyrimidine 206 CZPWVGJYEJSRLH-UHFFFAOYSA-N quinoline 207 SMWDFEZZVXVKRB-UHFFFAOYSA-N acetonitrile 208 WEVYAHXRMPXWCK-UHFFFAOYSA-N propionitrile 209 FVSKHRXBFJPNKK-UHFFFAOYSA-N n-butyronitrile 210 KVNRLNFWIYMESJ-UHFFFAOYSA-N 3-methylbutanenitrile 211 QHDRKFYEGYYIIK-UHFFFAOYSA-N Continued on next page

S4 Solvent ID InChIKey acrylonitrile 212 NLHHRLWOUZZQLW-UHFFFAOYSA-N phenylacetonitrile 213 SUSQOBVLVYHIEX-UHFFFAOYSA-N benzonitrile 214 JFDZBHWFFUWGJE-UHFFFAOYSA-N nitromethane 215 LYGJENNIWJXYER-UHFFFAOYSA-N nitroethane 216 MCSAJNNLRCFZED-UHFFFAOYSA-N 1-nitropropane 217 JSZOAYXJRCEYSX-UHFFFAOYSA-N 2-nitropropane 218 FGLBSLMDCBOPQK-UHFFFAOYSA-N nitrobenzene 219 LQNUZADURLCDLV-UHFFFAOYSA-N formamide 220 ZHNUHDYFZUAESO-UHFFFAOYSA-N N-methylformamide 221 ATHHXGZTWNVVOU-UHFFFAOYSA-N N,N-dimethylformamide 222 ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylthioformamide 223 SKECXRFZFFAANN-UHFFFAOYSA-N N,N-diethylformamide 224 SUAKHGWARZSWIH-UHFFFAOYSA-N N-methylacetamide 225 OHLUUHNLEMFGTQ-UHFFFAOYSA-N N,N-dimethylacetamide 226 FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-diethylacetamide 227 AJFDBNQQDYLMJN-UHFFFAOYSA-N 2-pyrrolidinone 228 HNJBEVLQSNELDL-UHFFFAOYSA-N N-methyl pyrrolidinone 229 SECXISVLQFMRJM-UHFFFAOYSA-N 1-methyl-2-pyrrolidinethione 230 OQILOJRSIWGQSM-UHFFFAOYSA-N tetramethylurea 231 AVQQQNCBBIEMEU-UHFFFAOYSA-N tetraethylurea 232 UWHSPZZUAYSGTB-UHFFFAOYSA-N dimethylcyanamide 233 OAGOUCJGXNLJNL-UHFFFAOYSA-N carbon disulfide 234 QGJOPFRUJISHPQ-UHFFFAOYSA-N dimethyl sulfide 235 QMMFVYPAHWMCMS-UHFFFAOYSA-N diethyl sulfide 236 LJSQFQKUNVCTIA-UHFFFAOYSA-N diisopropyl sulfide 237 XYWDPYKBIRQXQS-UHFFFAOYSA-N dibutyl sulfide 238 HTIRHQRTDBPHNZ-UHFFFAOYSA-N tetrahydrothiophene 239 RAOIDOHSFRTOEL-UHFFFAOYSA-N thiane 240 YPWFISCTZQNZAU-UHFFFAOYSA-N dimethylsulfoxide 241 IAZDPXIOMUYVGZ-UHFFFAOYSA-N dibutyl sulfoxide 242 LOWMYOWHQMKBTM-UHFFFAOYSA-N sulfolane 243 HXJUTPCZVOIRIF-UHFFFAOYSA-N thiobis(2-ethanol) 244 YODZTKMDCQEPHD-UHFFFAOYSA-N diethyl sulfite 245 NVJBFARDFTXOTO-UHFFFAOYSA-N dimethyl sulfate 246 VAYGXNSJCAHWJZ-UHFFFAOYSA-N diethyl sulfate 247 DENRZWYUOJLTMF-UHFFFAOYSA-N methanesulfonic acid 248 AFVFQIVMOAPDHO-UHFFFAOYSA-N trimethylphosphate 249 WVLBCYQITXONBZ-UHFFFAOYSA-N triethylphosphate 250 DQWPFSLDHJDLRL-UHFFFAOYSA-N tri-n-butylphosphate 251 STCOOQWBFONSKY-UHFFFAOYSA-N hexamethylphosphoric triamide 252 GNOIPBMMFNIUFM-UHFFFAOYSA-N hydrogen peroxide 253 MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen fluoride 254 KRHYYFGTRYWZRS-UHFFFAOYSA-N sulfuric acid 255 QAOWNCQODCNURD-UHFFFAOYSA-N ammonia 256 QGZKDVFQNNGYKY-UHFFFAOYSA-N hydrazine 257 OAKJQQAXSVQMHS-UHFFFAOYSA-N sulfur dioxide 258 RAHZWNYVWXNFOC-UHFFFAOYSA-N thionyl chloride 259 FYSNRJHAOHDILO-UHFFFAOYSA-N phosphorus oxychloride 260 XHXFXVLFKHQFAL-UHFFFAOYSA-N dihydrolevoglucosenone 261 WHIRALQRTSITMI-UJURSFKZSA-N Table S2: Solvent information.

S5 S3 Similarity regional dendrograms

glycerol

1,3-propanediol

hexamethylphosphoric triamide

0.00 0.05 0.10 0.15 0.20 SSI

Figure S1: Dendrogram for solvents to the left of node 1 in Figure 2.

S6 triethanolamine diethylene glycol 1,2-propanediol thiobis(2-ethanol) diethanolamine ethanol 1,4-butanediol 1,2-butanediol (2R,3S)-2,3-butanediol triethylene glycol benzyl alcohol 2-butanol 2-phenylethanol 2-methyl-1-propanol 2-methyl-2-butanol 1-octanol 1-decanol 1-dodecanol allyl alcohol 2-propanol 2-methyl-2-propanol 1-propanol 1-butanol 3-methyl-1-butanol 1-pentanol 1-hexanol cyclohexanol aminoethanol 2-methoxyethanol 2-ethoxyethanol methanol 1,5-pentanediol N-methylformamide ethylene glycol 0.00 0.02 0.04 0.06 0.08 SSI

Figure S2: Dendrogram for solvents to the left of node 2 in Figure 2.

S7 di-n-butylorthophthalate 1,8-cineole diisopropyl ether diethyl ether dibutyl ether di-n-propyl ether tetrahydropyran 2-methyltetrahydrofuran diethylene glycol dimethyl ether 1,2-dimethyoxyethane tri-(n-butyl)amine n-propyl acetate butyl acetate ethyl propionate methyl propionate isopentyl acetate 2,2,4,4-tetramethyl-3-pentanone diethyl sulﬁte diethyl carbonate 1,3-dioxolan methyl orthoformate methyl orthoacetate 1,3-dioxane methyl acetate diethyl malonate ethyl formate ethyl acetate pyrimidine methyl formate dimethyl carbonate dimethylphthalate cyclopentanone cyclohexanone 2-butanone 3-methyl-2-butanone 2-pentanone 3,3-dimethyl-2-butanone 3-pentanone 3-heptanone 2-heptanone 2,4,5-trimethylacetophenone quinoline cinnamaldehyde acetophenone 2-bromopyridine p-methoxybenzaldehyde 3-bromopyridine diphenyl ketone 4-methyl-2-pentanone ethyl phenyl ketone benzyl methyl ketone methyl benzoate butyraldehyde ethyl benzoate propionaldehyde ethyl acetoacetate diethyl sulfate bis(2-chloroethyl) ether benzaldehyde 0.00 0.01 0.02 0.03 0.04 0.05 0.06 SSI

Figure S3: Dendrogram for solvents to the left of node 3 in Figure 2.

S8 sulfolane

benzylamine

acetone

1-methyl-2-pyrrolidinethione

dimethylcyanamide

gamma-butyrolactone

dihydrolevoglucosenone

2,4-pentanedione

0.00 0.01 0.02 0.03 0.04 0.05 SSI

Figure S4: Dendrogram for solvents to the left of node 4 in Figure 2.

S9 pentanoic acid

hexanoic acid

butanoic acid

propanoic acid

pyrrole

0.00 0.01 0.02 0.03 0.04 0.05 0.06 SSI

Figure S5: Dendrogram for solvents to the left of node 5 in Figure 2.

S10 triethylamine tetraethylurea piperidine diethylamine di-n-butylamine pyridine 2-methylpyridine 2,6-dimethylpyridine 3-methylpyridine 2,4-dimethylpyridine 4-methylpyridine 2,4,6-trimethylpyridine n-butylamine N,N-dimethylacetamide N,N-diethylformamide N,N-dimethylformamide N-methylacetamide 2-pyrrolidinone tetrahydrofuran morpholine trimethylphosphate triethylphosphate tri-n-butylphosphate pyrrolidine dibutyl sulfoxide tetramethylurea N-methyl pyrrolidinone N,N-diethylacetamide 0.00 0.01 0.02 0.03 0.04 0.05 0.06 0.07 SSI

Figure S6: Dendrogram for solvents to the left of node 6 in Figure 2.

S11 ethylenediamine

dimethylsulfoxide

hydrazine

ethylene carbonate

4-methyl-1,3-dioxolan-2-one

ammonia

0.00 0.02 0.04 0.06 0.08 0.10 SSI

Figure S7: Dendrogram for solvents to the left of node 7 in Figure 2.

S12 para-cresol meta-cresol 2,4-dimethylphenol ortho-cresol 2-chloroethanol phenol 2,2,2-triﬂuoroethanol acetic acid 2-cyanoethanol heptanoic acid formic acid methanesulfonic acid phosphorus oxychloride nitroethane nitromethane sulfur dioxide o-chloroaniline 1,1,2-trichloroethane thionyl chloride 0.00 0.02 0.04 0.06 0.08 0.10 0.12 0.14 SSI

Figure S8: Dendrogram for solvents to the left of node 8 in Figure 2.

S13 aniline 2-methoxyphenol dimethyl sulfate 2,3-butanedione methylphenylamine n-butyronitrile 3-methylbutanenitrile propionitrile phenylacetonitrile p-chloroacetophenone benzonitrile acetic anhydride 2-cyanopyridine N,N-dimethylthioformamide acrylonitrile acetonitrile ethyl trichloroacetate benzoyl bromide benzoyl chloride nitrobenzene ethyl chloroacetate 1-nitropropane 2-nitropropane 1,2-dichloroethane 0.00 0.01 0.02 0.03 0.04 0.05 0.06 SSI

Figure S9: Dendrogram for solvents to the left of node 9 in Figure 2.

S14 toluene meta-xylene para-xylene ortho-xylene 1,3,5-trimethylbenzene 1,2,3,4-tetrahydronaphthalene isopropylbenzene ethylbenzene styrene benzene diphenyl ether furan thiane diethyl sulfide 1,2-dimethoxybenzene tetrahydrothiophene dimethyl sulfide ethyl phenyl ether anisole N,N-dimethylaniline diisopropyl sulfide dibutyl sulfide dibenzyl ether 0.00 0.01 0.02 0.03 0.04 0.05 SSI

Figure S10: Dendrogram for solvents to the left of node 10 in Figure 2.

S15 perfluorooctane perfluoroheptane n-perfluorohexane perfluoromethylcyclohexane cis-perfluorodecalin tetrachloroethylene carbon tetrachloride fluorobenzene chlorobenzene iodobenzene bromobenzene n-butyl iodide 1-bromobutane ortho-dichlorobenzene meta-dichlorobenzene 1,1,1-trichloroethane 1,2,4-trichlorobenzene hexafluorobenzene 1,4-dichlorobutane 1,1-dichloroethane trichloroethylene trans-1,2-dichloroethylene 1,2-dibromoethane methylene iodide 1,1,2,2-tetrachloroethane bromoform pentachloroethane chloroform dichloromethane dibromomethane 0.00 0.01 0.02 0.03 0.04 0.05 0.06 SSI

Figure S11: Dendrogram for solvents to the left of node 11 in Figure 2.

S16 n-pentane

cis-decalin

2-methylbutane

2,2,4-trimethylpentane

cyclohexane

n-octane

n-decane

n-hexadecane

n-dodecane

n-hexane

n-heptane

tetramethylsilane

carbon disulﬁde 0.0000 0.0025 0.0050 0.0075 0.0100 0.0125 0.0150 0.0175 0.0200 SSI

Figure S12: Dendrogram for solvents to the left of node 12 in Figure 2.

S17 hydrogen peroxide

formamide

water

0.000 0.025 0.050 0.075 0.100 0.125 0.150 0.175 0.200 SSI

Figure S13: Dendrogram for solvents to the left of node 13 in Figure 2.

S18 3-chlorophenol

1,1,1,3,3,3-hexaﬂuoro-2-propanol

triﬂuoroacetic acid

dichloroacetic acid

sulfuric acid

hydrogen ﬂuoride

0.000 0.025 0.050 0.075 0.100 0.125 0.150 0.175 0.200 SSI

Figure S14: Dendrogram for solvents to the left of node 14 in Figure 2.

S19