# C4H10O constitutional-isomer stability

Seven neutral, closed-shell gas-phase constitutional isomers were compared with AIMNet2-wB97MD3. For each isomer, RDKit ETKDG supplied eight starting geometries. The AMS Conformers tool optimized and ranked them with the same AIMNet2 model. Duplicate minima were removed by the Conformers defaults.

The table uses the electronic energy of the lowest-energy optimized conformer for each isomer. It contains no zero-point, thermal, enthalpic, entropic, or other vibrational correction. Relative energies share the minimum electronic energy of the seven isomers as their zero.

| Name                                      | SMILES    | Picture                                                 | Relative energy (kcal/mol)   |
|:------------------------------------------|:----------|:--------------------------------------------------------|:-----------------------------|
| 2-methylpropan-2-ol                       | CC(C)(C)O | <img src="figures/2_methylpropan_2_ol.png" width="180"> | 0.000                        |
| butan-2-ol                                | CCC(O)C   | <img src="figures/butan_2_ol.png" width="180">          | 3.114                        |
| 2-methylpropan-1-ol                       | CC(C)CO   | <img src="figures/2_methylpropan_1_ol.png" width="180"> | 5.408                        |
| butan-1-ol                                | CCCCO     | <img src="figures/butan_1_ol.png" width="180">          | 6.689                        |
| ethoxyethane (diethyl ether)              | CCOCC     | <img src="figures/ethoxyethane.png" width="180">        | 13.151                       |
| 2-methoxypropane (methyl isopropyl ether) | COC(C)C   | <img src="figures/2_methoxypropane.png" width="180">    | 13.675                       |
| 1-methoxypropane (methyl n-propyl ether)  | COCCC     | <img src="figures/1_methoxypropane.png" width="180">    | 15.789                       |

The lowest electronic energy in this calculation belongs to **2-methylpropan-2-ol**.

## Calculation details and provenance

Results were loaded directly from `01-conformers_workdir`. AIMNet2-wB97MD3 is trained against ωB97M-D3/def2-TZVPP reference data. The calculations used one process and one OpenMP thread per job, and the seven jobs ran sequentially.

The `Unique conformers` column in the CSV records how many distinct optimized structures remained from the eight initial geometries.

### butan-1-ol

Loaded because it provides the optimized conformers and electronic energies for `CCCCO`.

```ams
Generator
  Method RDKit
  RDKit
    InitialNConformers 8
  End
End

Task Generate

System
   Atoms
      C 2.139400258239331 -0.036055158052976426 0.42834912070057185
      C 0.7377085335077097 -0.6379910915294023 0.39272158052076334
      C -0.31174943833769186 0.4233163640891479 0.04378969993776187
      C -1.717479986329517 -0.18179596894541536 0.0091513981530556
      O -2.6577051371794687 0.7967632834026925 -0.3414066516042645
      H 2.1964673892463873 0.7638666535761252 1.197092639266751
      H 2.40224315610825 0.38884107657504263 -0.5638575389385778
      H 2.876892101265528 -0.8262023185132142 0.6828211842025563
      H 0.7150304619068395 -1.451407259248889 -0.3650488783243229
      H 0.5097513282647163 -1.0775563026932156 1.3883131354938523
      H -0.08103338074661472 0.8618192041587269 -0.9519710664497474
      H -0.28359035016605666 1.236168910237432 0.8023830318850932
      H -1.7539322132117119 -0.9918871762920326 -0.7502530160337909
      H -1.9731475780719911 -0.6252384390179516 0.9988444931244729
      H -2.7988551444956107 1.3573582222539187 0.4658639676301599
   End
   BondOrders
      1 2 1
      1 6 1
      1 7 1
      1 8 1
      2 3 1
      2 9 1
      2 10 1
      3 4 1
      3 11 1
      3 12 1
      4 5 1
      4 13 1
      4 14 1
      5 15 1
   End
End

Engine MLPotential
  Model AIMNet2-wB97MD3
EndEngine
```

### butan-2-ol

Loaded because it provides the optimized conformers and electronic energies for `CCC(O)C`.

```ams
Generator
  Method RDKit
  RDKit
    InitialNConformers 8
  End
End

Task Generate

System
   Atoms
      C 1.9534638542796732 0.13494166346342323 0.2239299605795384
      C 0.6254829106247907 -0.6024648862882708 0.06152482943762811
      C -0.5133770497883248 0.3534684378323693 -0.32666615727614856
      O -0.2477249541960441 0.9151418599615972 -1.5861072597591066
      C -1.8480749349079515 -0.39519770003269056 -0.37060899861978563
      H 1.8671800049804625 0.9180741105769555 1.0070163640400616
      H 2.7424369560569737 -0.584728615129754 0.5282224742763917
      H 2.257208310111546 0.6060623059143834 -0.7348308296984573
      H 0.3817523706923211 -1.101211142496629 1.0252223345987115
      H 0.7400485552750414 -1.3889751824208045 -0.7164391322324776
      H -0.5838175569923895 1.156658196634468 0.4443143172006574
      H -0.8187168665212655 1.7235784757524726 -1.6659485508162324
      H -1.8135661748082792 -1.2061912191413138 -1.1293943449648736
      H -2.666448981903221 0.30708821930545743 -0.636340701908322
      H -2.075846442903294 -0.8362445239316425 0.6232780645286802
   End
   BondOrders
      1 2 1
      1 6 1
      1 7 1
      1 8 1
      2 3 1
      2 9 1
      2 10 1
      3 4 1
      3 5 1
      3 11 1
      4 12 1
      5 13 1
      5 14 1
      5 15 1
   End
End

Engine MLPotential
  Model AIMNet2-wB97MD3
EndEngine
```

### 2-methylpropan-1-ol

Loaded because it provides the optimized conformers and electronic energies for `CC(C)CO`.

```ams
Generator
  Method RDKit
  RDKit
    InitialNConformers 8
  End
End

Task Generate

System
   Atoms
      C -1.0620660099146346 -1.1776703487091151 -0.40624749065400406
      C -0.07442596231173572 -0.2795251950999552 0.3479153591012813
      C -0.7797734306252334 0.9926894235501873 0.8366669585148669
      C 1.1290841255586763 0.06266696937359781 -0.544677965147703
      O 2.090193732858409 0.7672773978322973 0.19250828693046396
      H -1.9153396353675445 -1.4471239095121506 0.252263140113841
      H -0.5615997649553727 -2.11793990523889 -0.7219184595139064
      H -1.454063120747027 -0.6594458783985225 -1.3079245678621259
      H 0.2923793732110193 -0.8404779289434812 1.2361246246318924
      H -0.08045564421200276 1.6191905910813582 1.4298864911110476
      H -1.6382812377471205 0.7273691877380275 1.489996476590627
      H -1.15487986185779 1.5886139347693506 -0.023133651390819077
      H 1.5841157784902007 -0.878155010201341 -0.9288486460764126
      H 0.7959455518500651 0.6745468736963893 -1.413766814594425
      H 2.829166105770068 0.967983798062298 -0.43884374175463403
   End
   BondOrders
      1 2 1
      1 6 1
      1 7 1
      1 8 1
      2 3 1
      2 4 1
      2 9 1
      3 10 1
      3 11 1
      3 12 1
      4 5 1
      4 13 1
      4 14 1
      5 15 1
   End
End

Engine MLPotential
  Model AIMNet2-wB97MD3
EndEngine
```

### 2-methylpropan-2-ol

Loaded because it provides the optimized conformers and electronic energies for `CC(C)(C)O`.

```ams
Generator
  Method RDKit
  RDKit
    InitialNConformers 8
  End
End

Task Generate

System
   Atoms
      C 1.3919261545653183 -0.49855968447411725 -0.36691229641680045
      C 0.06255346265179593 -0.06023428060728956 0.263819190472406
      C -1.0867563941734633 -0.8951013873265391 -0.3309647087354302
      C -0.1687468161851669 1.4363290958136976 -0.01632795643903783
      O 0.14342974903325395 -0.2794064032784371 1.651892495620742
      H 1.3773749778574687 -0.34427788418975186 -1.4676791242116376
      H 2.233922921502832 0.08659104296536506 0.061709212946711646
      H 1.579800772615245 -1.574658204620469 -0.16248198757130922
      H -1.1376458820298745 -0.7642775174729393 -1.4335766946325565
      H -0.9354936687258333 -1.9730007983271702 -0.10736346262219068
      H -2.0605967735353885 -0.5835960602201198 0.10413239650707348
      H -0.19411699008840771 1.6319584841901802 -1.1101941625239748
      H -1.1337080994150894 1.7703859235121373 0.4218108851641604
      H 0.6457853638042205 2.0429119248013623 0.4346036483718059
      H -0.7177287778769461 0.004935749234065989 2.057532564070049
   End
   BondOrders
      1 2 1
      1 6 1
      1 7 1
      1 8 1
      2 3 1
      2 4 1
      2 5 1
      3 9 1
      3 10 1
      3 11 1
      4 12 1
      4 13 1
      4 14 1
      5 15 1
   End
End

Engine MLPotential
  Model AIMNet2-wB97MD3
EndEngine
```

### ethoxyethane (diethyl ether)

Loaded because it provides the optimized conformers and electronic energies for `CCOCC`.

```ams
Generator
  Method RDKit
  RDKit
    InitialNConformers 8
  End
End

Task Generate

System
   Atoms
      C -2.3526389539768324 -0.2139694416503115 0.5697967583752033
      C -1.1723787819236078 -0.07263793235072921 -0.37905594753593236
      O 0.021553262092716217 -0.01737692734038376 0.37196364364573486
      C 1.121254500278169 0.11385472735118297 -0.5032467378781906
      C 2.4037489479540124 0.17276415759707958 0.31225758683961785
      H -2.2516554869854066 -1.1457528233143734 1.165878739635729
      H -3.2983369124655977 -0.2584820106969855 -0.01067129989002422
      H -2.3932090978494123 0.6567062510246358 1.258280456650741
      H -1.1694771498770382 -0.9511057834437485 -1.0641822727340813
      H -1.3117545848254635 0.8605969972797174 -0.9713052396989168
      H 1.1864185417564066 -0.7595492698278558 -1.191746207365161
      H 1.0441408277591855 1.0521531397967177 -1.0988654930009425
      H 3.276472241971319 0.2761079222790427 -0.36667049538958557
      H 2.3771556472194515 1.0445749924635603 0.9999857557434254
      H 2.5187069988720916 -0.7578839991675372 0.9075807526023766
   End
   BondOrders
      1 2 1
      1 6 1
      1 7 1
      1 8 1
      2 3 1
      2 9 1
      2 10 1
      3 4 1
      4 5 1
      4 11 1
      4 12 1
      5 13 1
      5 14 1
      5 15 1
   End
End

Engine MLPotential
  Model AIMNet2-wB97MD3
EndEngine
```

### 1-methoxypropane (methyl n-propyl ether)

Loaded because it provides the optimized conformers and electronic energies for `COCCC`.

```ams
Generator
  Method RDKit
  RDKit
    InitialNConformers 8
  End
End

Task Generate

System
   Atoms
      C 2.494008186586153 -0.18022399072973494 0.6657971961216024
      O 1.4253783312345611 0.5228083056867531 0.07282334466564667
      C 0.2136178154818576 -0.14588444948344628 0.3511224699623995
      C -0.9383146123422644 0.6226525625337175 -0.2950138334957292
      C -2.2792895519897654 -0.055166916954231135 -0.027363612926140996
      H 2.3867361064887485 -0.21856469394955974 1.7727880214840783
      H 3.4384634810050296 0.3557610478155286 0.439289197583619
      H 2.5823021445044594 -1.2077116495504314 0.24761142181575385
      H 0.2317128206028298 -1.1786609424773586 -0.06806596350123134
      H 0.03696236308964691 -0.1936400854667544 1.4507522680837905
      H -0.7735867150525935 0.6815067082098518 -1.3929018811143319
      H -0.9664679204450332 1.6570782677791565 0.11134560893350649
      H -2.2825563434832485 -1.0838003816044834 -0.44687063752699013
      H -2.476394720068454 -0.10338926729782853 1.064839523554201
      H -3.092571385612161 0.5272354854888018 -0.509360024075812
   End
   BondOrders
      1 2 1
      1 6 1
      1 7 1
      1 8 1
      2 3 1
      3 4 1
      3 9 1
      3 10 1
      4 5 1
      4 11 1
      4 12 1
      5 13 1
      5 14 1
      5 15 1
   End
End

Engine MLPotential
  Model AIMNet2-wB97MD3
EndEngine
```

### 2-methoxypropane (methyl isopropyl ether)

Loaded because it provides the optimized conformers and electronic energies for `COC(C)C`.

```ams
Generator
  Method RDKit
  RDKit
    InitialNConformers 8
  End
End

Task Generate

System
   Atoms
      C 1.9657678197789905 -0.31942175593683336 -0.5243323995000491
      O 0.6871543744766825 0.1492260103638603 -0.8934255294354574
      C -0.18586369516253184 0.1547204056320169 0.22360795014235746
      C -1.071106735445375 1.3978996572278406 0.1409077767683169
      C -1.0507683218146333 -1.1091662450620612 0.20594795275711278
      H 2.4605723481968527 0.39364537603450284 0.17131759162427426
      H 1.912966223735056 -1.3330100629033736 -0.06894193337405194
      H 2.593413581474101 -0.39176255755949335 -1.4360587160630198
      H 0.34997606868399167 0.204519708338424 1.2033513901300292
      H -0.43774140941449785 2.310063675131042 0.16386168681206334
      H -1.6584984093156228 1.3966591446381291 -0.8024723239415854
      H -1.7698195210736059 1.4343222938262012 1.0041283244668933
      H -1.7649135869207508 -1.100087283929636 1.0570252551355326
      H -0.41038389633657 -2.0108647362824246 0.30058336393828183
      H -1.6207548408620696 -1.176743629518205 -0.7455003894606549
   End
   BondOrders
      1 2 1
      1 6 1
      1 7 1
      1 8 1
      2 3 1
      3 4 1
      3 5 1
      3 9 1
      4 10 1
      4 11 1
      4 12 1
      5 13 1
      5 14 1
      5 15 1
   End
End

Engine MLPotential
  Model AIMNet2-wB97MD3
EndEngine
```