This WELIWATTE_readme20221004.txt file was generated on 20221004 by Nipunika Samali Perera Weliwatte.

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GENERAL INFORMATION
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1. Title of Dataset 
Dataset for: Three-stage conversion from chemically inert n-heptane to α-hydrazino aldehyde based on bioelectrocatalytic C-H bond oxyfunctionalization

2. Author Information

  Principal Investigator Contact Information
        Name: Shelley D. Minteer
        Institution: Department of Chemistry, University of Utah
        Address: 315 South 1400 East, RM B611, TBBC (Thatcher Bld) Salt Lake City, Utah 84112, USA
        Email: minteer@chem.utah.edu

  Associate or Co-investigator Contact Information
        Name: N. Samali Weliwatte
        Institution: Department of Chemistry, University of Utah
        Address: 315 South 1400 East, RM 202, Salt Lake City, Utah 84112, USA
        Email: u1143728@chem.utah.edu

  Associate or Co-investigator Contact Information
        Name: Hui Chen
        Institution: Department of Chemistry, University of Utah
        Address: 315 South 1400 East, RM 202, Salt Lake City, Utah 84112, USA
        Email: Chen.Hui@utah.edu

  Associate or Co-investigator Contact Information
        Name: Tianhua Tang, 
        Institution: Department of Chemistry, University of Utah
        Address: 315 South 1400 East, RM 202, Salt Lake City, Utah 84112, USA
        Email: tianhua.tang@utah.edu

Alternate Contact Information
        Name: Shelley D. Minteer
        Institution: Department of Chemistry, University of Utah
        Address: 315 South 1400 East, RM B611, TBBC (Thatcher Bld) Salt Lake City, Utah 84112, USA
        Email: shelley.minteer@utah.edu

3. Date of data collection (single date, range, approximate date) 
20210301-20220731

4. Geographic location of data collection (where was data collected?): 
Department of Chemistry, University of Utah, Salt Lake City, Salt Lake County, Utah, USA

5. Information about funding sources that supported the collection of the data: 
The Office of Naval Research (Grant #N00014-21-1-4008)
National Science Foundation Center for Synthetic Organic Electrochemistry (CHE2002158)
The Army Research Office MURI (Grant#W911NF-14-1-0263)


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SHARING/ACCESS INFORMATION
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1. Licenses/restrictions placed on the data: 
Open Access


2. Links to publications that cite or use the data: Weliwatte, N. Samali, Chen Hui, Tang Tianhua, Minteer, Shelley D. 2022. Three-stage conversion from chemically inert n-heptane to α-hydrazino aldehyde based on bioelectrocatalytic C-H bond oxyfunctionalization, ACS Catalysis. 


3. Links to other publicly accessible locations of the data: None


4. Links/relationships to ancillary data sets: None


5. Was data derived from another source? No
           If yes, list source(s): None


6. Recommended citation for the data: Weliwatte, N. Samali, Chen Hui, Tang Tianhua, Minteer, Shelley D. 2022. Dataset for: "Three-stage conversion from chemically inert n-heptane to α-hydrazino aldehyde based on bioelectrocatalytic C-H bond oxyfunctionalization." ACS Catalysis. The Hive: University of Utah Research Data Repository. https://doi.org/10.7278/S50d-m87v-xesj 


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DATA & FILE OVERVIEW
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1. File List
   A. Filenames:   
      Short description: Folder "Biocatalysis Step (Step 2)" contains the GC data files for the biocatalytic step. Data filenames in folder "Biocatalysis Step (Step 2)": 
662. 30 mins T3.txt
667. 90 mins T1.txt
670. 120 mins T1.txt
672. 0 mins T1.txt
705. 30 mins T2.txt
706. 30 mins T1.txt
711. 45 mins T1.txt
717. 120 mins T2.txt
720. 0 mins T3.txt
722. 15 mins T1.txt
733. 45 mins T2.txt
734. 45 mins T3.txt
735. 60 mins T1.txt
738. 120 mins T3.txt
739. 15 mins T3.txt
740. 15 mins T2.txt
742. 0 mins T2.txt
769. 60 mins T2.txt
770. 60 mins T3.txt                   

        
   B. Filenames:  
      Short description: Folder "Controls" contains the GC data files for the control steps. Data filenames in folder "Controls":
117. Control 1 ml air.txt
125. Control without AQ-LPEI.txt
220. Blank (without AlkG).txt
222. Blank (without AlkG).txt
223. Blank (without AQ-LPEI).txt
224. Blank (without AQ-LPEI).txt

        
   C. Filenames:
      Short description: Folder "Organocatalysis Step (Step 3)" contains the GC data files for the control steps. Data filenames in folder "Organocatalysis Step (Step 3)":
756. Blank.txt
820. Without Buffer and Extra. DCM 20 % 15 hours.txt
821. Without Buffer and Extra. DCM 20 % 15 hours.txt
822. Without Buffer and Extra. DCM 20 % 15 hours I.txt
823. With Buffer and Extra. DCM 20 % 15 hours I.txt
824. With Buffer and Extra. DCM 20 % 15 hours I.txt
825. With Buffer and Extra. DCM 20 % 15 hours II.txt
826. With Buffer and Extra. DCM 20 % 15 hours II.txt
827. With Enzymes, Buffer and Extra. DCM 20 % 15 hours II.txt
828. With Enzymes, Buffer and Extra. DCM 20 % 15 hours II.txt
829. With Enzymes, Buffer and Extra. DCM 20 % 15 hours II.txt
830. With Enzymes, Buffer and Extra. DCM 20 % 15 hours II.txt
831. With Enzymes, Buffer and Extra. DCM 20 % 15 hours III.txt
832. With Enzymes, Buffer and Extra. DCM 20 % 15 hours III.txt
833. With Enzymes, Buffer and Extra. DCM 20 % 15 hours IV.txt
834. With Enzymes, Buffer and Extra. DCM 20 % 15 hours IV.txt
835. Without Buffer and Extra. DCM 20 % 15 hours IV.txt

   D. Filenames:   
      Short description: Folder "Parameter Optimization (Step 1)" contains the GC data files for the control steps. Data filenames in folder "Parameter Optimization (Step 1)":
121. Step 1 Air injection 2.5 ml 2 hrs.txt
122. Step 1 Air injection 2.5 ml 2 hrs.txt
163. 1to1 alkG and alkB 2.5 ml T1.txt
164. 1to1 alkG and alkB 2.5 ml T2.txt
165. 1to1 alkG and alkB 2.5 ml T3.txt
172. Step 1 Air injection 2.5 ml 2 hrs.txt
186. Step 1 Air injection 2.5 ml 2 hrs.txt
187. Step 1 Air injection 2.5 ml 2 hrs.txt
203. Step 1 Applied Potential -0.65 V.txt
204. Step 1 Applied Potential -0.65 V.txt
247. Step 1 Applied Potential -0.65 V.txt
248. Step 1 Applied Potential -0.65 V.txt
251. Step 1 Applied Potential -0.7 VT1.txt
255. Step 1 Applied Potential -0.7 VT3.txt
255. Step 1 Applied Potential -0.7 V.txt
340. Step 1 Applied Potential -0.75 VT2.txt
341. Step 1 Applied Potential -0.75 V.txt
343. Step 1 Applied Potential -0.85 V.txt
344. Step 1 Applied Potential -0.85 VT1.txt  
345. Step 1 Applied Potential -0.8 V.txt
346. Step 1 Air injection 4 ml T4.txt
347. Step 1 Applied Potential -0.85 VT2.txt
348. Step 1 Applied Potential -0.8 VT3.txt
350. Step 1 Air injection 3 ml T1.txt
351. Step 1 Air injection 3.5 ml T2.txt
353. Step 1 Air injection 2 ml T2.txt
354. Step 1 Air injection 3 ml T2.txt
355. Step 1 Air injection 3.5 ml T2.txt
356. Step 1 Air injection 3.5 ml T1.txt
358. Step 1 Air injection 4 ml T2.txt
359. Step 1 Air injection 4 ml T2.txt
363. Step 1 Air injection 2 ml T3.txt
364. Step 1 Air injection 3 ml T3.txt
365. Step 1 Air injection 3.5 ml T3.txt
366. Step 1 Air injection 4 ml T2.txt
367. Step 1 Air injection 4 ml T3.txt
368. Step 1 Air injection 2 ml T4.txt
369. Step 1 Air injection 3.5 ml T3.txt
370. Step 1 Air injection 3.5 ml T3.txt
381. Step 1 Time -0.8 V 3 hr T3.txt
382. Step 1 Time -0.8 V 4 hr T1.txt
383. Step 1 Time -0.8 V 4 hr T3.txt 
387. Step 1 Time -0.8 V 1 hr T4.txt
388. Step 1 Time -0.8 V 1 hr T5.txt
389. Step 1 Time -0.8 V 1 hr T6.txt
392. Step 1 Time -0.8 V 2 hr T4.txt
393. Step 1 Time -0.8 V 2 hr T5.txt
394. Step 1 Time -0.8 V 3 hr T4.txt
395. Step 1 Time -0.8 V 2 hr T6.txt
396. Step 1 Time -0.8 V 3 hr T5.txt
406. Step 1 Time -0.8 V 4 hr T8.txt
414. Step 1 Applied Potential -0.75 VT6.txt
603. Step 1 Applied Potential -0.8 V.txt
607. Step 1 Applied Potential -0.8 V.txt

   E. Filenames:  
      Short description: Folder "Standard GCs" contains the GC data files for the control steps. Data filenames in folder "Standard GCs":
173. 1 mM 1-heptanol WC
174. 0.5 mM 1-heptanol WC
175. 2 mM 1-heptanol WC
176. 5 mM 1-heptanol WC
177. 10 mM 1-heptanol WC
178. 0.5 mM heptanal WC
179. 0.5 mM heptanal WC
180. 1 mM heptanal WC
181. 2 mM heptanal WC
182. 5 mM heptanal WC
183. 5 mM heptanal WC
282. 0.5 mM Heptanol.txt
283. 1 mM Heptanol.txt
284. 2 mM Heptanol.txt
285. 5 mM Heptanol.txt
286. 10 mM Heptanol.txt
287. 5 mM Heptanol.txt
288. 0.5 mM Heptanal.txt
289. 1 mM Heptanal.txt
290. 2 mM Heptanal.txt
291. 5 mM Heptanal.txt
292. 0.5 mM Heptanal.txt
293. 10 mM Heptanal.txt
315. 1 mM 1-Heptanol T3.txt
317. 0.5 mM 1-Heptanol T3.txt
318. 1 mM 1-Heptanol T3.txt
319. 2 mM 1-Heptanol T3.txt
320. 2 mM 1-Heptanol T3.txt
321. 5 mM 1-Heptanol T3.txt
322. 5 mM 1-Heptanol T3.txt
323. 1 mM 1-Heptanol T3.txt
324. 0.5 mM 1-Heptanol T4 H.txt
332. 1 mM 1-Heptanol T5 H.txt
333. 0.5 mM 1-Heptanol T5 H.txt
334. 2 mM 1-Heptanol T5 H.txt
335. 5 mM 1-Heptanol T5 H.txt
336. 10 mM 1-Heptanol T5 H.txt
836. 5 mM IS Step 3.txt
837. 0.25 mM IS Step 3.txt
838. 0.25 mM IS Step 3.txt
839. 0.5 mM IS Step 3.txt
840. 0.5 mM IS Step 3.txt
841. 1 mM IS Step 3.txt
842. 1 mM IS Step 3.txt
843. 2 mM IS Step 3.txt
844. 5 mM IS Step 3.txt


2. Relationship between files:    Contains GC data pertaining to the bulk electrolytic experiments, organocatalytic reaction, and standards used in the study. The standard GC files calibrate the sensitivity of the column in the Gas Chromatograph to 1-heptanol, heptanal, and the corresponding alpha-hydrazino aldehyde. This information is used to quantify the peaks of 1-heptanol and heptanal obtained in the bulk electrolytic experiments and the alpha-hydrazino aldehyde obtained in the organocatalytic step.

3. Additional related data collected that was not included in the current data package: 
All the other relevant data collected in this study have been compiled into a manuscript and a supporting information file that are under review to be published in a peer-reviewed journal.

4. Are there multiple versions of the dataset? No



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METHODOLOGICAL INFORMATION
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1. Description of methods used for collection/generation of data: 
Experiments were carried out using an Agilent 5975C that was equipped with a DB-5MS column (30 m × 0.25 mm × 0.25 μm) and a triple-axis detector. The inlet temperature was held at 240 °C with a 1.2 mL/min column flow rate and helium as the carrier gas. For the GC-MS analysis of step I and step II, the generated alcohol and aldehyde were extracted with MTBE containing 1 mM eicosane as an internal standard. 2 µL samples were manually injected onto the column. For the GC analysis of 1-heptanol, 1-octanol, benzyl alcohol, 2-phenylethanol, heptanal, octanal, benzaldehyde, and phenylacetaldehyde, the oven temperature was held at 60 °C for 1 minute followed by a ramp to 200 °C at a rate of 20 °C/min, and held at 200 °C for 15 min. For the GC analysis of hexanol and hexanal, the oven temperature was held at 60 °C for 5 min and ramped to 200 °C at a rate of 10 °C/min. For the GC-MS analysis of step III, the generation of imines, the reactions were stopped by adding aqueous NaOH (10% v/v, 10 N). The generated imines were extracted with MTBE containing 1 mM eicosane as an internal standard. 2 µL samples were manually injected onto the column. For the GC method for imine analysis, the oven temperature was kept at 60 °C for 1 minute followed by a ramp to 200 °C at a rate of 20 °C/min, and held at 200 °C for 15 min.  

2. Methods for processing the data: 
GC (Gas Chromatography) results of the standard solutions of known concentrations were used to construct working curves for 1-heptanol (generated in Step 1), heptanal (generated in Step 2) and alpha-hydrazino aldehyde (generated in Step 3). The peak area of each species obtained from each experiment and respective working curves were used to determine the concentration of each species in each GC injection. The resulting values were used to calculate the concentrations of each species in each experimental cell.

3. Instrument- or software-specific information needed to interpret the data: 
Chromeleon Chromatography Data System Software, v. 7.3.1

4. Standards and calibration information, if appropriate: 
As mentioned in response 2, calibration for each chemical species (i.e., 1-heptanol, heptanal, alpha-hydrazino aldehyde) was conducted by using five concentrations of each stock solution. 1-heptanol and heptanal were purchased from Sigma Aldrich. The alpha-hydrazino aldehyde stock solution was synthesized according to literature reports.

5. Environmental/experimental conditions: None


6. Describe any quality-assurance procedures performed on the data: Triplicates of each data set were obtained.


7. People involved with sample collection, processing, analysis and/or submission: N Samali Weliwatte, Hui Chen, Tianhua Tang, Shelley D. Minteer